A kind of preparation method of chiral compound 2,2-dimethyl-3-(oxirane-2-yl) methyl propionate
A technology of chiral compounds and ethylene oxide, applied in organic chemistry methods, organic chemistry and other directions, to achieve the effects of easy conditions, readily available raw materials, and simple process operations
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0022] Present embodiment S-2, the synthetic route of 2-dimethyl-3-(oxirane-2-yl) methyl propionate is as follows:
[0023]
[0024] (1) Synthesis of 2,2-dimethyl-3-(oxirane-2-yl) methyl propionate (compound a)
[0025] Add n-butyllithium (48ml, n-hexane solution with a molar concentration of 2.5M) dropwise at -78°C to a solution of diisopropylamine (12.21g, 120.63mmol) in tetrahydrofuran (50ml), and raise the temperature to 0°C after dropping Stir for 30min, then cool the reaction solution to -78°C, slowly add methyl isobutyrate (11.20g, 109.66mmol) dropwise to the reaction solution, and stir at -78°C for 2h after dropping, add glycidyl p-toluenesulfonate Tetrahydrofuran solution (50ml) of ester (31.04g, 135.98mmol, (2S)-(+)-Glycidyl tosylate) was added dropwise to the reaction solution. After the drop was completed, the temperature was slowly raised to 25°C and stirred overnight. After the reaction was detected, saturated chlorine was added. Ammonium chloride aqueous sol...
Embodiment 2
[0032] Present embodiment S-2, the synthetic route of 2-dimethyl-3-(oxirane-2-yl) methyl propionate is as follows:
[0033]
[0034] (1) Synthesis of 2,2-dimethyl-3-(oxirane-2-yl) methyl propionate (compound a)
[0035] Add n-butyllithium (129.24ml, n-hexane solution with a molar concentration of 2.5M) dropwise at -78°C to a solution of diisopropylamine (32.7g, 323.11mmol) in tetrahydrofuran (150ml) and heat up to 0 ℃ and stirred for 30min, then cooled the reaction solution to -78℃, slowly added methyl isobutyrate (30g, 293.73mmol) into the reaction solution dropwise, and stirred at -78℃ for 2h after dropping, and epoxybromopropane (48.28 g, 352.48mmol) of tetrahydrofuran solution (50ml) was added dropwise to the reaction solution, and after the drop was completed, the temperature was slowly raised to 25°C and stirred overnight, and the reaction was detected to be complete. Extract and combine the organic phases, wash the organic phase with saturated saline solution (100ml...
Embodiment 3
[0039] Present embodiment S-2, the synthetic route of 2-dimethyl-3-(oxirane-2-yl) methyl propionate is as follows:
[0040]
[0041] (1) Synthesis of 2,2-dimethyl-3-(oxirane-2-yl) methyl propionate (compound a)
[0042] Add n-butyllithium (48ml, n-hexane solution with a molar concentration of 2.5M) dropwise at -78°C to a solution of diisopropylamine (12.21g, 120.63mmol) in tetrahydrofuran (50ml), and raise the temperature to 0°C after dropping Stir for 30min, then cool the reaction solution to -78°C, slowly add methyl isobutyrate (11.20g, 109.66mmol) dropwise into the reaction solution, and stir at -78°C for 2h after dropping, add m-nitrobenzenesulfonic acid Glycidyl ester (34g, 134.99mmol, (S)-(+)-Glycidylnosylate) tetrahydrofuran solution (50ml) was added dropwise to the reaction solution, after the drop was completed, the temperature was slowly raised to 25°C and stirred overnight, and the reaction was detected to be complete, and saturated chlorine was added Ammonium c...
PUM
| Property | Measurement | Unit |
|---|---|---|
| optical purity | aaaaa | aaaaa |
| optical purity | aaaaa | aaaaa |
Abstract
Description
Claims
Application Information
Login to View More