Water → MS-1254

Reaction equation

C[O-].[Na+].[CH3:4][O:5][C:6](=[O:9])[CH2:7][SH:8].Cl[CH2:11][C:12](=[O:14])[CH3:13].O>CO>[CH3:4][O:5][C:6](=[O:9])[CH2:7][S:8][CH2:11][C:12](=[O:14])[CH3:13]

Participants

Procedure

To a mixture of a 5.4 M methanolic solution of sodium methylate (185 mL, 1.00 mol) in 500 mL methanol is added mercapto-acetic acid methyl ester (97.0 g, 912 mmol) at RT. After stirring for 20 minutes at RT chloro acetone (80 mL, 1.0 mmol) is added carefully. After complete addition the reaction mixture is heated at reflux for 20 minutes. The reaction mixture is added to water and extracted with diethyl ether. The organic layer is washed with brine, dried over Na2SO4 and the solvent is evaporated under reduced pressure. The crude reaction product is distilled under reduced pressure (75° C.-90° C., 0.3 mbar) yielding the desired product as colorless liquid. Yield: 61.5 g. (M+H)+=163