4-Toluenesulfonyl chloride → (2R)-2-(4-Chlorophenyl)-2-cyclopropylethyl 4-methylbenzenesulfonate

Participants

Reaction Steps

(2R)-2-(4-Chlorophenyl)-2-cyclopropylethanol (6.50 g, 33.0 mmol), tosyl chloride (7.86 g, 41.0 mmol) and 6.0 ml of triethylamine (6.0 ml) are dissolved in dichloromethane (150 ml) and allowed to stir for 3 days. The reaction mixture is washed successively with 1 N HCl (100 ml), water (100 ml) and saturated brine solution (100 ml). The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel eluting with ether:hexane (10:90 to 25:75) to afford the title compound as a colorless oil (11.1 g, 96%) which is characterized by 1HNMR, 13CNMR and mass spectral analysis.

Provenance & Evidence