Reaction #595321

Reaction equation

Cyclopropanesulfonyl chloride

BuOH

pyridine

→

oil

Yield 71.0%

Butyl cyclopropanesulfonate

Yield 71.0%

Conditions

Workup

1. 1
   TemperatureThe mixture was slowly warmed at room temperature
2. 2
   OtherThe solvent was removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe resulting white solid was dissolved in CHCl3
4. 4
   WashThe organic phase was washed with water, brine
5. 5
   Dryingdried (MgSO4)
6. 6
   Concentrationconcentrated

Procedure

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), 0.93 (t, 3H).

Source