Ethyl 1-(methylthiomethyl)cyclopropanecarboxylate → 1-[(Methylsulfanyl)methyl]cyclopropane-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A 50% solution of sodium hydroxide (2.0 mL, 38 mmol, 7.8 equiv) was added to a stirred solution of ethyl 1-(methylthiomethyl)cyclopropanecarboxylate (860 mg, 4.9 mmol, 1.0 equiv) in absolute ethanol (10 mL) at 23° C. The resulting solution was stirred at 23° C. for 20 h. The reaction mixture was diluted with a 0.5M solution of sodium hydroxide (100 mL) and washed with dichloromethane (3×100 mL). The aqueous layer was acidified to pH≈1 with concentrated hydrochloric acid and extracted with dichloromethane (4×100 mL). The combined organic layers were dried (Na2SO4), gravity-filtered, and concentrated by rotary evaporation to afford a light brown oil (420 mg, 58%): 1H NMR (300 MHz, CDCl3) δ 2.82 (s, 2H), 2.17 (s, 3H), 1.41 (dd, J=7, 4 Hz, 2H), 0.99 (dd, J=7, 4 Hz, 2H).

Provenance & Evidence