4-Toluenesulfonyl chloride → HCID 178472496, compound

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To a solution of cis/trans-4-(2-hydroxy-1-hydroxymethyl-ethoxy)-cyclohexanecarboxylic acid ethyl ester (3:7) (0.74 g, 3.0 mmol) and triethylamine (0.42 ml, 3.0 mmol) in dichloromethane (30 ml) a catalytic amount of 4-N,N-dimethylaminopyridine was added. A solution of p-toluenesulfonyl chloride (0.57 g, 3.0 mmol) in dichloromethane (10 ml) was added dropwise at room temperature. Stirring for 16 h was followed by partitioning between ethyl acetate (100 ml) and 0.5 M aqueous hydrogen chloride solution (50 ml). The layers were separated. The aqueous layer was extracted with two portions of ethyl acetate. The combined organic layers were washed with one portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.46 g, 38%) as colorless oil. MS m/e: 401 (M+H+)

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