Methanol → HCID 53808805, compound

Participants

Reaction Steps

Sodium (7.09 g, 308 mmol) in methanol (100 ml) was added over 35 min to a stirred solution of (R)-2-bromo-3-hydroxypropanoic acid (25.5 g, 151 mmol) in methanol (200 ml) at -25°. The temperature was allowed to reach 10° and the mixture stirred for a further 2 h. 2-Propanethiol (11.4 ml, 240 mmol) in sodium methoxide solution, prepared from sodium (5.68 g, 247 mmol) and methanol (100 ml) was added to this suspension (240 ml, 120 mmol) at -5°. After 16 h at room temperature the solvent was evaporated and the residue dissolved in water/ether/conc. hydrochloric acid to a final pH of approximately 1. The organic phase was separated and the aqueous phase re-extracted with ether (×2). The combined organic extracts were dried (Na2SO4) and the solvent evaporated to give the sub-title compound (18.56 g).

Provenance & Evidence