Water → 3-(4-Methylphenyl)sulfonyl-1-tetrahydropyranyloxypropane

Participants

Reaction Steps

32 g (144 mmol) of 3-bromo-1-tetrahydropyranyloxypropane (1a) are dissolved in 200 ml of 1,2-dimethoxyethane, 26.9 g (151 mmol) of anhydrous sodium 4-methylphenyl-sulfinate, 4.5 g (14 mmol) of tetrabutylammoniumbromide and 1.05 g (7 mmol) of sodium iodide are added and the mixture is heated to boiling for 24 hours. After cooling, 500 ml of water are added, the mixture is extracted with three times 300 ml of dichloromethane each time, the combined dichloromethane extracts are washed with water and dried with magnesium sulfate. After filtering off the drying agent and distilling off the solvent in vacuo a yellowish brown oil is obtained which is purified by column chromatography (silica gel; dichloromethane or dichloromethane/ethyl acetate mixtures). 32.5 g (76%) of a colorless oil are isolated, which partly crystallizes on prolonged standing (m.p.<30° C.)

Provenance & Evidence