1-Butanol → Butyl cyclopropanesulfonate

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).

1. customThe solvents were removed under reduced pressure
2. customthe residue was partitioned between DCM and water (50 mL each)
3. washThe organic phase was further washed with brine (40 mL)
4. dry with materialdried over anhydrous MgSO4 and concd under reduced pressure

ORD record

ord-87e007b70b6a4892a2dac8a2c70d4e4c

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426411B2