Acetic Acid → Ethyl 2-(mercaptomethyl)butanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of the thioester of Step 1 (5.00 g, 24.5 mmol) in MeOH (15 mL) at 0° C., under nitrogen, was added K2CO3 (9.67 g, 73.5 mmol). The resulting mixture was stirred at 0° C. for a half hour, and then AcOH (8.82 g, 147 mmol) and 25% aq NH4OAc were added. The title compound was extracted with EtOAc, dried over Na2SO4 and purified by distillation on a Kugelrohr apparatus (200° C., 760 mm Hg). Yield: 1.700 g, 45%. 1H NMR (CD3COCD3): δ 0.86 (3H, t), 1.25 (3H, t), 1.65 (2H, quintet), 1.78 (1H, t), 2.45 (1H, quintet), 2.68 (2H, m), 4.15 (2H, q).

Provenance & Evidence