Category: 13831-03-3

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.

A dry, argon-filled Schlenk tube with a magnetic stirrer bar and septum is initially charged with tert-butyl prop-2-ynoate (70 mg, 0.56 mmol) in anhydrous THF (2 ml). After adding (TMP)2Zn.MgCl2 (2.2 ml, 1.2 mmol) at 25C, the mixture is stirred for 30 min, then a solution of l -fluoro-3-iodobenzene (160 mg, 0.72 mmol), tetrakis(triphenylphosphine)palladium(0) (33 mg, 5 mol%>) in anhydrous THF (2 ml) is added dropwise and the mixture is stirred at 25C overnight. For workup, the mixture is diluted with aqueous sat. NH4CI solution (30 ml) and extracted with ethyl acetate (3 x 30 ml). After the combined organic phases have been dried over Na2S04, the solvent has been distilled off and purification has been effected by column chromatography on silica gel (heptane : ethyl acetate), the desired compound (91 mg, 75% of theory) was obtained as a colourless oil. ? NMR (400 MHz, CDC13): delta in ppm = 7.34 (m, 2H), 7.26 (m, 1H), 7.13 (m, 1H), 1.53 (s, 9H) Preparation of ethyl 4-(2-chloro-

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

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; BAYER CROPSCIENCE AG; FORD, Mark, James; MOSRIN, Marc; WO2013/120911; (2013); A1;,
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13831-03-3, Name is tert-Butyl propiolate, 13831-03-3, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Step 3: 1 -[4-(tert-Butyl-dimethyl-silanyloxymethyl)-benzyl]-1 H-[1 ,2,3]triazole-4- carboxylic acid tert-butyl ester. Cupric sulfate pentahydrate (1 .03 g, 4.1 1 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 50ml 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 DCM. The organic layer is separated and concentrated under reduced pressure to obtain the crude title compound (Yield 8.3 g). LC (Method 4): tR = 0.73 min; Mass spectrum (ES+): m/z = 404 [M+H]+.

Statistics shows that tert-Butyl propiolate is playing an increasingly important role. we look forward to future research findings about 13831-03-3.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FRATTINI, Sara; BAKKER, Remko; GIOVANNINI, Riccardo; HAMPRECHT, Dieter; LINGARD, Iain; PAUTSCH, Alexander; WELLENZOHN, Bernd; (92 pag.)WO2017/72020; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 13831-03-3, name is tert-Butyl propiolate, 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. 13831-03-3

General procedure: A Schlenk tube (25 cm3) equipped with a magnetic stir barwas charged with terminal alkyne (1.2 mmol), (i-Pr)2EtN(1.5 mmol), CuBr¡¤SMe2 (0.1 mmol), TBPAc (0.3 mmol),oxirane (2.0 mmol), and 2.0 cm3 MeCN. After the mixturewas stirred at 25 C for 1 h, propiolate (1.0 mmol) wasadded under an inert atmosphere. The tube was evacuatedand backfilled with argon (three times). Subsequently, themixture was stirred for 16 h at appropriate temperature (seeTables 2, 3). After cooling to room temperature, the mixturewas passed through silica gel pad and concentrated underreduced pressure. The resulting residue was purified with column chromatography on silica gel (eluent gradient ofEtOAc/hexane, see spectroscopic analysis section) to givethe corresponding products 4 in the yields listed in Tables 2and 3.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of tert-Butyl propiolate.

Reference:
Article; Jahanshad, Milad; Manafi, Mohammadreza; Mousavi-Safavi, Seyed Mahmoud; Homami, Seyed Saied; Ghazanfarpour-Darjani, Majid; Monatshefte fur Chemie; vol. 151; 1; (2020); p. 113 – 122;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

13831-03-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 13831-03-3, name is tert-Butyl propiolate, This compound has unique chemical properties. The synthetic route is as follows.

To ethyl cyanoformate (10 g, 101.01 mmol) was added NH2OH-HCl (8.4 g, 121.74 mmol), K2CO3 (19.9 g, 144.20 mmol), and CH2C12/H2O (100 mL). The resulting mixture was stirred for 12 hr at room temperature. The solids were filtered out and the filtrated was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :1), resulted in 6 g (45%) of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate as a white solid. To a mixture of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate (1 g, 7.58 mmol) and tert-butyl propiolate (940 mg, 7.46 mmol) was added Et3N (765 mg, 7.57 mmol) and toluene (50 mL). The resulting solution was stirred at 140 0C for 1 min. The resulting mixture was washed with 50 mL of H2O and then was extracted with 3 x 50 mL of dichloromethane. The organic layers were combined and washed with 20 mL of brine, then dried over anhydrous sodium sulfate. Evaporated the solvents and the residue was purified onto a silica gel column with ethyl acetate/petroleum ether (1 :1), resulted in 1.1 g (61%) of 5 -tert-butyl 2-ethyl lH-imidazole-2, 5-dicarboxylate as a yellow solid.

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Reference:
Patent; PONIARD PHARMACEUTICALS, INC.; WO2009/139834; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics