Acetic Acid → HCID 86688089, compound

Participants

Reaction Steps

Crude (R)-2-(benzyloxy)-2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid (13 g, 46 mmol) was dissolved in CH2Cl2 (150 mL) and cooled in an ice bath. Ethanethiol (6.9 mL, 93 mmol) and N,N-dimethylpyridin-4-amine (0.11 g, 0.93 mmol) were added followed by DCC (11 g, 56 mmol). This mixture was stirred in ice bath and allowed to slowly warm to ambient temperature overnight. Acetic acid (15 mL) was added and the reaction was stirred for 10 minutes. The reaction mixture was poured into vigorously stirring ether (400 mL) and then filtered. The filtrate was washed with 10% sodium carbonate, water, 0.5 N HCl, water, brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified over silica gel (1-5% EtOAc in hexanes) to afford (R)—S-ethyl 2-(benzyloxy)-2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethanethioate (2.3 g, 7.1 mmol, 15% yield) as a yellow oil.

Provenance & Evidence