Ethyl Thioglycolate → Tert-butyl 2-(ethoxycarbonylmethylthiomethyl)acrylate

To a stirred solution of ethyl α-mercaptoacetate (1.6 g) in ethanol (15 ml), potassium tert-butoxide (1.5 g) was added at -10°-0° C. under nitrogen atmosphere, and the mixture was stirred for 10 minutes at room temperature. Under ice-cooling, tert-butyl 2-bromomethylacrylate (2.9 g) dissolved in ethanol (5 ml) was added to the reaction mixture and the mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 2.1 g (60%) of tert-butyl 2-(ethoxycarbonylmethylthiomethyl)acrylate.

1. temperatureUnder ice-cooling
2. additionwas added to the reaction mixture
3. stirringthe mixture was stirred for 1 hour at room temperature
4. concentrationThe reaction mixture was concentrated in vacuo
5. dissolutionthe residue was dissolved in ethyl acetate
6. washThe solution was washed with water and saturated sodium chloride solution
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated in vacuo
9. customThe oily residue was purified by a silica gel column chromatography

ORD record

ord-dbea497b333d4270847f6cce9aa0b889

Source dataset

uspto-grants-1994_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05292767