1-Butanol → Butyl cyclopropanesulfonate

Participants

Reaction Steps

To a solution of cyclopropanesulfonyl chloride (5.00 g, 35.6 mmol) in n-BuOH (20 mL) at −20° C., pyridine (5.75 mL, 71.1 mmol) was added dropwise. The resulting mixture was stirred for about 16 h while warming slowly to ambient temperature. The solvents were removed under reduced pressure and the residue was partitioned between DCM and water (50 mL each). The organic phase was further washed with brine (40 mL), dried over anhydrous MgSO4 and concd under reduced pressure to yield butyl cyclopropanesulfonate (4.7 g, 74%) as a yellow oil. 1H NMR (DMSO-d6) δ 4.2 (t, 2H), 2.82 (m, 1H), 1.64 (m, 2H), 1.35 (m, 2H), 1.08 (m, 2H), 1.01 (m, 2H), 0.89 (t, 3H).

Provenance & Evidence