Tetrahydrofuran → Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A 1M solution of lithium aluminum tri-tert-butoxyhydride in tetrahydrofuran (70.90 mL, 70.90 mmol) was added to a stirred solution of diethyl cyclopropane-1,1′-dicarboxylate (6 g, 32.20 mmol) in tetrahydrofuran (129 mL) at 23° C. The resulting solution was heated to 65° C. and stirred for 24 h. The cooled reaction mixture was diluted with a 10% solution of sodium bisulfate (275 mL) and extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to give the desired product as a pale yellow oil (4.60, 91%): 1H NMR (300 MHz, CDCl3) δ 4.16 (q, J=7 Hz, 2H), 3.62 (s, 2H), 2.60 (br s, 1H), 1.22-1.30 (m, 5H), 0.87 (dd, J=7, 4 Hz, 2H).

Provenance & Evidence