Pyridine → 4-(Methoxymethoxy)cyclohexane 1,1-dimethyl dimethanesulfonate

Reaction equation

[CH3:1][O:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][C:8]([CH2:13][OH:14])(CO)[CH2:7][CH2:6]1.N1C=CC=CC=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:1][O:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH3:21][S:22]([O:14][CH3:13])(=[O:24])=[O:23].[CH3:21][S:22]([O:14][CH3:13])(=[O:24])=[O:23]

Participants

Procedure

6.84 g of 4-(methoxymethoxy)cyclohexane-1,1-dimethanol was dissolved in 110 ml of dichloromethane and 13.56 g of pyridine was added thereto and ice-cooled. 7.79 ml of methanesulfonyl chloride was added thereto and the resulting mixture was stirred at room temperature for 17 hours. Then the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 11.91 g of the title compound as a colorless oily substance.