Category: 13831-03-3

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13831-03-3, name is tert-Butyl propiolate, A new synthetic method of this compound is introduced below., Computed Properties of C7H10O2

To the mixture of methyl 3-iodobenzoate (157 mg, 0.60 mmol), potassium carbonate (166mg, 1.20 mmol), cupper(I) iodide (14 mg, 0.07 mmol) and PdC12(Ph3P)2 (21 mg, 0.03 mmol) in tetrahydroffiran (2 mE) was added tert-butyl propiolate (330 pL, 2.40 mmol) at room temperature. Afier stirred for 20 h at 60 C., the mixture was evaporated to dryness. Theresidue was chromatographed on a silica gel (EtOAc:hex- anes=0: 1 -1 :10) to give the title compound 9-1(155 mg, 99%yield) as a light brown oil.?H NMR (300 MHz, CDC13) oe 8.25 (t, J=1.4, 1H), 8.16- 8.05 (m, 1H), 7.80-7.68 (m, 1H), 7.46 (t, J=7.8, 1H), 3.93 (s,3H), 1.55 (s, 9H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; The Broad Institute, Inc.; Massachusetts General Hospital; Hung, Deborah; Stanley, Sarah; Kawate, Tomohiko; Iwase, Noriakie; Shimizu, Motohisa; (32 pag.)US9416121; (2016); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13831-03-3, name is tert-Butyl propiolate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 13831-03-3, name: tert-Butyl propiolate

n-Butyllithium (1.6 M in hexane; 41.9 mL, 67.0 mmol) was added dropwise within 10mm at -55 to -50CC to a soln of tert-butyl propiolate (103; 8.76 mL, 63.8 mmol) in dryTHF (200 mL). The mixture was allowed to stir at -40C for 1.5 h. The mixture wascooled to -78C. A soln of 102 (7.25 g, 31 9 mmol) in THF (66 mL) was added within 10 mm with the temperature not exceeding -64C. The mixture was stirred for 0.5 h at-78C, then warmed to -40C and allowed to slowly warm to 0C over 3 h. The mixture was poured into 1 M aq. KHSO4 soln and extracted with EtOAc. The organicphase was dried (Na2SO4) and concentrated. FC (hexane/EtOAc 90:10 to 70:30) afforded the ketone 104 (8.34 g, 89%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl propiolate, and friends who are interested can also refer to it.

Reference:
Patent; POLYPHOR AG; OBRECHT, Daniel; ERMERT, Philipp; OUMOUCH, Said; PIETTRE, Arnaud; GOSALBES, Jean-Francois; THOMMEN, Marc; WO2013/139697; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 13831-03-3, A common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Preparation of Copper Acetylides; Procedure 1To a solution of CuI (3.8 g, 20.0 mmol) in a mixture of NH4OH(28% NH3 solution, 50 mL) and EtOH (30 mL) was added the alkyne1 (10.0 mmol) dropwise. The deep blue reaction mixture wasstirred overnight at r.t. under argon and the yellow precipitate wascollected by filtration and successively washed with NH4OH (10%NH3 solution, 3 × 50 mL), H2O (3 × 50 mL), EtOH (3 × 50 mL), andEt2O (3 × 50 mL). The bright yellow solid was then dried under highvacuum overnight to afford the desired polymeric copper acetylide2, which was used without further purification.

The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Theunissen, Cedric; Lecomte, Morgan; Jouvin, Kevin; Laouiti, Anouar; Guissart, Celine; Heimburger, Jeremy; Loire, Estelle; Evano, Gwilherm; Synthesis; vol. 46; 9; (2014); p. 1157 – 1166;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 13831-03-3, A common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a suspension of copper(I) iodide (335 mg) in tetrahydrofuran (100 mL) was added t-butyl prpiolate (3.63 mL), diisopropylethylamine (4.62 mL) and a solution of 5(R)-azidomethyl-3-[4-(1-cyanocyclopropan-1-yl)phenyl]oxazolidin-2-one (5.00 g) in tetrahydrofuran (10 mL), the mixture was stirred at room temperature for 2.5 hours, and then concentrated in vacuo. After dilution of the residue with ethyl acetate, the resulting precipitates were filtered off, and then concentrated in vacuo. Treatment of the residue with ethyl acetate gave t-butyl 1-[5(R)-3-[4-(1-cyanocyclopropan-1-yl)phenyl]-2-oxooxazolidin-5-ylmethyl]-1,2,3-triazole-4-carboxylate (6.85 g). [0423] MS (EI+) m/z: 409 (M+). [0424] HRMS (EI+) for C21H23N5O4 (M+): calcd, 409.1750; found, 409.1729.

The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fukuda, Yasumichi; US2003/225107; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: tert-Butyl propiolate

0.2mmol added benzenesulfonyl hydrazide in the reactor, 0.2mmol of t-butyl propiolate, 5.0 mol% palladium acetate, 5.0 mol% dppp, 0.4 mmol copper acetate, 15 mol% beta-aminopropionic acid,2.0mL DMF and DMAc mixed solvent (volume ratio [3: 1]). In a nitrogen atmosphere, heat to 80 C and continue stirring for 0.5h to stop the reaction and cool to room temperature.Washed with saturated NaCl, then extracted with ethyl acetate, dried,The solvent was removed by distillation under reduced pressure, and the crude product was separated by column chromatography to obtain the target product with a yield of 78%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13831-03-3, its application will become more common.

Reference:
Patent; Hunan University; Zhou Yongbo; Liu Lixin; Su Lebin; Dong Jianyu; Yin Shuangfeng; (9 pag.)CN110698368; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13831-03-3, name is tert-Butyl propiolate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 13831-03-3, Product Details of 13831-03-3

General procedure: To a stirred solution of the acetylenic ester (2 mmol) and the 1,3-diketones (2 mmol) in 10 mL of CH2Cl2 was added 0.26 g of isoquinoline (2 mmol) at r.t. After completion of the reaction (2-3 h), as indicated by TLC (AcOEt/hexane, 1:2), the solvent was removed under reduced pressure and the viscous residue was purified by column chromatography on silica gel (Merck 230-400 mesh) using hexane-AcOEt (2:1) as eluent to afford pure title compounds.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, tert-Butyl propiolate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Piltan, Mohammad; Yavari, Issa; Moradi, Loghman; Journal of the Iranian Chemical Society; vol. 13; 4; (2016); p. 605 – 608;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 13831-03-3,Some common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred solution of 3-butyl-3-ethyl-8-hydroxy-2-methyl-7-(methylthio)-5-phenyl-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine 1,1-dioxide (Intermediate 152; 200 mg, 0.46 mmol) in dry THF (3 mL), DABCO (5.10 mg, 0.05 mmol) and tert butyl propiolate (0.1 mL, 0.7 mmol) were added at room temperature, and the reaction mixture was stirred for 1 hour at room temperature. After completion of the reaction (monitored by LCMS), the reaction mixture was diluted with ice-cold water (10 mL). The aqueous layer was extracted with EtOAc (2¡Á10 mL). The combined organic layer was dried over anhydrous Na2SO4 and evaporated under vacuum. The resulting crude material was purified by Isolera column chromatography (eluent: 6% EtOAc in hexane; silica gel: 230-400 mesh) to afford the title compound. Yield: 75% (190 mg, white solid). H NMR (400 MHz, DMSO-d6): delta 7.61 (d, J=12.4 Hz, 1H), 7.38 (t, J=8.0 Hz, 3H), 7.30 (d, J=7.6 Hz, 2H), 7.12 (t, J=7.2 Hz, 1H), 6.46 (s, 1H), 5.31 (d, J=12.4 Hz, 1H), 4.12 (s, 2H), 2.88 (s, 3H), 2.08 (s, 3H), 1.92-1.86 (m, 1H), 1.82-1.76 (m, 1H), 1.55-1.43 (m, 10H), 1.19-1.08 (m, 5H), 0.83-0.62 (m, 6H). LCMS: (Method A) 505.2 (M+-tBu+H), Rt. 3.65 min, 97.40%.

The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Albireo AB; Gillberg, Per-Goeran; Mattsson, Jan; Starke, Ingemar; Kulkarni, Santosh S.; (152 pag.)US2019/367467; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 13831-03-3 as follows. Application In Synthesis of tert-Butyl propiolate

To a stirred solution of 3-butyl-3-ethyl-8-hydroxy-2-(4-methoxybenzyl)-7-(methylthio)-5-phenyl-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine 1,1-dioxide (Intermediate 128, 1.0 g, 1.85 mmol) in THF (10 mL) were added DABCO (0.02 g, 0.18 mmol) and t-butyl propiolate (0.28 g, 2.22 mmol) at 0 C. and the reaction mixture was stirred for 1 hour at room temperature. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with EtOAc (20 mL). The organic layer was washed with water (2¡Á15 mL), dried over anhydrous Na2SO4 and concentrated under vacuum. The resulting crude was purified by Isolera column chromatography (eluent: 15% EtOAc in hexane; silica gel: 230-400 mesh) to afford the title compound. Yield: 49% (0.6 g, white solid). 1H NMR (400 MHz, DMSO-d6): delta 7.66 (d, J=12.3 Hz, 1H), 7.43 (s, 1H), 7.37 (t, J=7.6 Hz, 2H), 7.26 (d, J=8.6 Hz, 2H), 7.20-7.14 (m, 3H), 6.87 (d, J=8.6 Hz, 2H), 6.48-6.25 (m, 1H), 5.27 (d, J=12.1 Hz, 1H), 4.51 (s, 2H), 4.30-4.10 (m, 2H), 3.73 (s, 3H), 2.08 (s, 3H), 1.50-1.36 (m, 13H), 1.18-0.84 (m, 4H), 0.72-0.48 (m, 6H). LCMS: (Method A) 611.2 (M+-tBu+H), Rt. 3.94 min, 98.16% (max).

According to the analysis of related databases, 13831-03-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Albireo AB; Gillberg, Per-Goeran; Mattsson, Jan; Starke, Ingemar; Kulkarni, Santosh S.; (152 pag.)US2019/367467; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13831-03-3, name is tert-Butyl propiolate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 13831-03-3, COA of Formula: C7H10O2

The methyl 5-chloro-2-(3-fluorophenyl)nicotinate (1.00 g, 3.76 mmol) was combined with freshly prepared 2-[(aminooxy)sulfonyl]-l,3,5-trimethylbenzene (0.972 g, 4.52 mmol) ether solution in acetonitrile (20.0 rnL) at room temperature. The reaction was stirred for 24 hours and became a tan colored slurry. The slurry was added portion wise to a vigorously stirring suspension of tert-butyl propiolate (1.55 mL, 1 1.3 mmol), N,N-dimethylformamide (20.0 mL, 258 mmol) and potassium carbonate (2.60 g, 18.8 mmol) open to the air. After stirring for 15 minutes, the reaction was a dark red brown suspension. This was allowed to stir for 5 hours at room temperature. The reaction was taken up in ethyl acetate and decanted from the solids. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give the crude product as a reddish brown oil. The product was purified on silica gel eluting hexane: ethyl acetate gradient to give 3-tert-butyl 6-methyl 4- chloro-7-(3-fluorophenyl)pyrazolo[l,5-a]pyridine-3,6-dicarboxylate (0.46 g, 30%) as a semisolid residue. LCMS calculated for C2oH19ClF 204 (M+H)+: m/z = 405.1 ; found: 404.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl propiolate, and friends who are interested can also refer to it.

Reference:
Patent; INCYTE CORPORATION; COMBS, Andrew P.; SPARKS, Richard B.; YUE, Eddy W.; WO2011/130342; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

13831-03-3,Some common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 9 Methyl (E)-3-[[1-(pyridin-3-yl)naphthalen-2-yl]oxy]acrylate 1-(Pyridin-3-yl)naphthalen-2-ol (80 mg, 0.26 mmol) obtained in Example 8 (1) was dissolved in dimethylformamide (2 mL), sodium hydride (16 mg, 0.4 mmol) was added thereto in an ice bath, and the solution was stirred at room temperature. After 10 minutes, methyl propiolate (91 muL, 1.1 mmol) was added to the reaction solution and the reaction solution was further stirred at 110 C. After 16 hours, water was added to the reaction solution in an ice bath, extraction was carried out using chloroform, the organic layer was dried over sodium sulfate and filtered, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate_hexane=1:2) to obtain a crude material of methyl (E)-3-[[1-(pyridin-3-yl)naphthalen-2-yl]oxy]acrylate (25 mg, yield of 22%) and methyl (Z)-3-[[1-(pyridin-3-yl)naphthalen-2-yl]oxy]acrylate. j0682] A title compound (white crystal, 24 mg, yield of41%) was obtained according to the same method as inExample 9 using 4-(2-mercaptonaphthalen- 1 -yl)benzonitrile(40 mg, 0.15 mmol) obtained in Example 48 (3) and t-butylpropiolate (63 pL, 0.46 mmol).10683] ?H NMR (CDC13, 400 MHz): oe=1.43 (s, 9H), 5.46(d, 1H, J=15 Hz), 7.32 (d, 1H, J=8 Hz), 7.4-7.5 (m, 3H),7.5-7.6 (m, 2H), 7.63 (d, 1H, J=8 Hz), 7.78 (d, 2H, J=8 Hz),7.9-8.0 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl propiolate, its application will become more common.

Reference:
Patent; J-Pharma Co., Ltd.; Endo, Tsuyoshi; Kobayashi, Kunio; Tanaka, Hiroto; Saito, Daisuke; Hirano, Masaharu; Endou, Hitoshi; Anzai, Naohiko; (68 pag.)US2017/290795; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics