[CH:1]1([O:4][CH2:5][CH2:6][CH2:7][OH:8])[CH2:3][CH2:2]1.ClCCl.C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([O:8][CH2:7][CH2:6][CH2:5][O:4][CH:1]2[CH2:3][CH2:2]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1
To a mixture of 500 mg of 3-(cyclopropyloxy)propan-1-ol and 5 mL of dichloromethane were added 1.2 mL of triethylamine and 1.3 g of p-toluenesulfonic acid chloride under ice-cooling, followed by stirring for 4 hours. The reaction mixture was diluted with chloroform, washed with 1 M hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 522 mg of 3-(cyclopropyloxy)propyl p-toluenesulfonate.
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