Water → HCID 18669129, compound

Participants

Reaction Steps

To a solution of 2-(cyclopentyloxy)-1-ethanol (prepared as described in J. Org. Chem., 1968, 33, 2271-2284: 127 mg, 0.97 mmol) and triethylamine (101 mg, 0.1 mmol) in dichloromethane (3 mL) at 0° C. was added 4-bromobenzenesulfonyl chloride (255 mg, 0.1 mmol) in dichloromethane (2 mL) dropwise over 5 minutes. The reaction was then warmed to room temperature and stirred for 16 hours. The mixture was then poured into water (3 mL) and the two layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give a crude residue. This was purified by column chromatography on silica gel (50 g), eluting with a gradient of dichloromethane:hexane (50:50 to 0:100), to give the title compound (200 mg, 59%) as a colourless oil.

Provenance & Evidence