Category: 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. SDS of cas: 13831-03-3

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

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., Safety of tert-Butyl propiolate

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, Safety of 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

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., Formula: C7H10O2

Lithium bis(trimethylsilyl)amide (4.95 mL, 4.95 mmol, 1.0 M in THF, 1.55 equiv.) was cooled to -78 C, then i-butyl propiolate (604 mg, 4.789 mmol, 1.5 equiv.) in 3 mL THF was added and the reaction mixture was stirred for 45 min. The solution was then added via cannula over 10 min to ketone (3R)-9 (953 mg, 3.193 mmol, 1 equiv.) in 5 mL THF at -78 C and stirred for 2 h. The reaction was quenched with satd aq NH4Cl (50 mL), warmed to rt, and extracted with EtOAc (4 x 50 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation. Purification by silica flash chromatography (50%? 100% CH2Cl2 in hexanes) yielded the ester (15,3R)-10 as a clear viscous oil (1.05 g, 78%). IR (ATR): 3400, 2956, 2932, 2888, 2860, 2248, 1710, 1473, 1395, 1371, 1258, 1204, 1153, 1114, 1039, 1013, 909, 888, 838, 781, 751, 732, 695, 672, 657. 1H-NMR (500 MHz; CDCl3): delta 7.63-7.60 (m, 1H), 7.47-7.45 (m, 2H), 7.38-7.37 (m, 1H), 5.19 (dd, 7 = 8.0, 6.3 Hz, 1H), 2.96 (d, 7 = 2.3 Hz, 1H), 1.49 (s, 9H), 0.95 (s, 9H), 0.24 (s, 6H). 13C-NMR (126 MHz; CDCl3): delta 151.8, 139.5, 139.1, 130.9, 130.3, 124.9, 124.4, 124.2, 84.2, 80.6, 78.2, 74.9, 74.4, 28.0, 25.7, 18.2, -4.65, -4.84. 19F-NMR (471 MHz; CDCl3): delta delta -115.05 (d, 7 = 224.7 Hz, 1F), -128.46 (d, 7 = 224.6 Hz, 1F). HRMS (ESI) m/z calcd for C22H30O4F2SiNa ([M+Na]+) 441.1779; found 441.1785.

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

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; TAN, Derek, Shieh; EVANS, Christopher, E.; SHARMA, Indrajeet; TONGE, Peter, James; MATARLO, Joe, S.; (242 pag.)WO2017/59411; (2017); 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, SDS of cas: 13831-03-3

(ii) Di-tert-butyl 8,8′-(((5-(2,2-dimethyl-4,20-dioxo-3,8,11,14,17-pentaoxa-5,21-diazatetracos-23-yn-24-yl)-1,3-phenylene)bis(methylene))bis(oxy))(11S,11aS,11’S, 11a’S)-bis(7-methoxy-2-methylene-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,11,11a-tetrahydro-H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate) (28) A catalytic amount of Pd(PPh3)4 (23.0 mg, 19.5 mumol) was added to a mixture of the iodoaryl compound 2a (1.02 g, 0.89 mmol), Boc-acetylene 27 (393 mg, 0.98 mmol), CuI (7.4 mg, 39.1 mumol), diethylamine (2.02 mL, 1.43 g, 19.5 mmol) and oven-dried 4 A molecular sieve pellets in dry DMF (9 mL) in an oven-dried sealable vessel. The mixture was degased and flushed with argon 3 times then heated in a microwave at 100 C. for 26 minutes at which point analysis by LC/MS revealed substantial product formation at retention time 1.89 minutes (ES+) m/z 1446 ([M+Na]+, ?100% relative intensity, 1424 ([M+H]+, ?15% relative intensity). The reaction mixture was allowed to cool to room temperature and was then filtered through a sinter to remove the sieves (washed with DMF). The filtrate was evaporated in vacuo and the resulting residue dissolved in DCM (100 mL) and washed with H2O (20 mL), brine (30 mL), dried (MgSO4), filtered and evaporated in vacuo to give the crude product. Purification by flash chromatography (gradient elution in 1% increments: 100% DCM to 97:3 v/v DCM/MeOH) provided the alkyne 28 as a yellow foam (882 mg, 70% yield).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; HOWARD, Philip Wilson; FLYGARE, John A.; PILLOW, Thomas; WEI, Binqing; US2014/294868; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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., SDS of cas: 13831-03-3

(1.0 mmol) of 1- (4′-bromophenyl) -2,2,2-trifluoroethanone (1.0 mmol), t-butyl propiolate (1.0 mmol),t-butylpropiolateAg2CO3(0.05 mmol), KOH (0.1 mmol) and DMA (1 mL) were added to Xu Linke bottles and thereaction was stirredatroom temperature for 24 h. The reaction was followed by TLC.After completion of the reaction, 15 mL of saturated brine was added to quench the reaction, antishall reaction mixture was extracted with dichloromethane (15 mL × 3) the product, the organic phases were combined, and concentrated using a rotary evaporator to give crude productproduct column chromatography to obtain the target The product, eluting with column chromatography, was petroleum ether: ethyl acetate (100: 1) and the product structure wasidentifiedbyNMR and high resolution mass spectrometry.1l isolated yield of 44%, 2l isolated yield of 43%.

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; Shihezi University; Liu Ning; Dai Bin; Wang Lei; (8 pag.)CN106432171; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application 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.

Hexamethylphosphoric triamide (10.7 g, 59.9 mmol) was dissolved in tetrahydrofuran (160 mL) under nitrogen(0.5 M, 36 mL) was added at 0 C for 0.5 hour at 0 C, tert-butyl propiolate (5.04 g, 40 mmol) was added and the reaction was continued for 1 hour. Then add 2b (5.47g, 40mmol), gradually rose to room temperature, reaction 5 hours, slowly adding 1M hydrochloric acid to the reaction solution, adjust the reaction solution pH to 2 ~ 3, The organic phase was washed with saturated brine (100 mL x 1), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography and purified. The organic phase was extracted with ethyl acetate (50 mL x 2) (Ethyl acetate: petroleum ether (v / v) = 0: 1 to 1: 9) to give the title compound 2c as a yellow oil (2.2 g, yield 21%).

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; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Wei Yonggang; Qiu Guanpeng; Lei Bolin; Li Yao; Wang Song; Zhu Guozhi; (39 pag.)CN106279128; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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., Quality Control of tert-Butyl propiolate

General procedure: Into an oven-dried reaction flask under Ar gas protection was added oxabicyclic alkene (0.2 mmol), Au catalyst (0.001 mmol), methyl propiolate (0.4 mmol) and toluene (1.0 mL). The reaction mixture was stirred at room temperature normally overnight. After complete consumption of the starting materials, monitored by TLC, the solvent was removed under reduced pressure and the residue was purified by flash column chromatography.

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

Reference:
Article; Sun, Yin-Wei; Xu, Qin; Shi, Min; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1969 – 1976;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference 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.

Oupric sulfate pentahydrate (1 .03 g, 4.11 mmol) and sodium ascorbate (4.07 g, 20.6 mmol) are added to a stirred solution of (4-Azidomethyl-benzyloxy)-tert-butyl-dimethy-silane (6.0 g, 20.6 mmol) and tert-butyl propiolate (3.10 ml, 22.6 mmol) dissolved in a mixture of 50 mL of tert-butanol and 50m1 of water. The reaction mixture is stirred at room temperature for 2 hours. The solvent is removed under reduced pressure and the residue is partitioned between water and DOM. The organic layer is separated and concentrated under reduced pressure to obtain thecrude title compound (yield 8.3 g).LO (Method 4): tR = 0.73 mm; Mass spectrum (ES+): m/z = 404 [M+H].

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FRATTINI, Sara; BAKKER, Remko; GIOVANNINI, Riccardo; FOSSATI, Giacomo; HAMPRECHT, Dieter; LINGARD, Iain; PAUTSCH, Alexander; WELLENZOHN, Bernd; (168 pag.)WO2017/72021; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 13831-03-3, 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.

To the mixture of methyl 3-iodobenzoate (157 mg, 0.60 mmol), K2CO3 (166 mg, 1.20 mmol), cupper(I) iodide (14 mg, 0.07 mmol) and PdCl2(Ph3P)2 (21 mg, 0.03 mmol) in tetrahydrofuran (2 mL) was added tert-butyl propiolate (16) (330 mL, 2.40 mmol) at room temperature. After stirred for 20 h at 60C, the mixture was evaporated to dryness. The residue was chromatographed on a silica gel (AcOEt:hexanes=0:1~1:10) to give tert-butyl 3-(3-(methoxycarbonyl)phenyl)propiolate (17b) (155 mg, 99% yield) as light brown oil. 1H NMR (300 MHz, CDCl3) delta 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).

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:
Article; Kawate, Tomohiko; Iwase, Noriaki; Shimizu, Motohisa; Stanley, Sarah A.; Wellington, Samantha; Kazyanskaya, Edward; Hung, Deborah T.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 22; (2013); p. 6052 – 6059;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics