Methanesulfonyl chloride → (S)-3-Fluoroheptyl Methanesulfonate

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Reaction Steps

To a 100 ml flask were added 8.7 g of (S)-3-fluoroheptanol and 21.5 g of pyridine under a nitrogen atmosphere, and the solution was kept at 5° to 10° C. To the solution was added dropwise 7.5 g of methanesulfonyl chloride over 30 minutes, followed by stirring at 15° C. or less for 5 hours. The reaction mixture was poured into 200 ml of ice-water and extracted with ethyl acetate. The organic layer was washed successively with a diluted hydrochloric aqueous solution and water, dried over magnesium sulfate, and the solvent was removed by distillation at 30° C. or lower to obtain 12.7 g (yield=93.18%) of the titled compound. NMR (ppm): 0.92 (3H, t, J=7.1 Hz), 1.35-1.8 (6H, m), 2.03 (2H, m), 3.02 (3H, s), 4.37 (1H, t, J=6.2 Hz), 4.65 (2H, m)

Provenance & Evidence