Methanol → Methyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

1,1-Cyclopropane dicarboxylic acid-1-methyl ester (4 g, 27.8 mmol) was mixed with DIPEA (6 ml, 34.4 mmol) in THF (50 ml) and stirred at a 0° C. for 10 min. To the reaction was slowly added ethyl chloroformate (2.7 ml, 28.1 mmol). The reaction was stirred for 1.5 hours and allowed to warm to ambient temperature. The reaction was then re-cooled to 0° C. and NaBH4 (1.6 g, 42.3 mmol) was slowly added, followed by the addition of methanol (3 ml, 74.2 mmol). The reaction was allowed to warm to ambient temperature over 2 h. Then the reaction was diluted with EtOAc and water. The aqueous layer was separated and extracted with EtOAc three times. The combined organic layers were washed with water, then brine, dried over (MgSO4), filtered, and concentrated to afford the title compound. 1H NMR (500 MHz, CDCl3): δ 3.70 (s, 3H), 3.60 (s, 2H), 1.25 (m, 2H), 0.85 (m, 2H).

Provenance & Evidence