1-Butanol → Butyl cyclopropanesulfonate

Temperature

-10 °C

Cyclopropanesulfonyl chloride (5 g, 35 mmol, 1 eq) was dissolved in an excess BuOH (20 ml), the reaction mixture was cooled at −10° C. and pyridine (5.8 mL, 70 mmol, 2 eq) was slowly added dropwise. The mixture was slowly warmed at room temperature and stirred overnight. The solvent was removed under reduced pressure and the resulting white solid was dissolved in CHCl3. The organic phase was washed with water, brine and dried (MgSO4) and concentrated to give an oil (4.8 g, 24.9 mmol, 71%). 1H NMR (300 MHz, CDCl3): δ 4.25 (t, 2H), 2.46 (m, 1H), 1.74 (m, 2H), 1.45 (m, 2H), 1.25 (dd, 2H), 1.09 (dd, 2H), 93 (t, 3H).

1. temperatureThe mixture was slowly warmed at room temperature
2. customThe solvent was removed under reduced pressure
3. dissolutionthe resulting white solid was dissolved in CHCl3
4. washThe organic phase was washed with water, brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated

ORD record

ord-f93bcc193765440ea9dd7eada4782451

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829052B2