3,4-dihydro-2H-pyran → (2RS)-1-O-(2-Tetrahydropyranyl)-2-O-(5-methyl-3-isoxazolyl)glycerol

Participants

Reaction Steps

A solution of 11.26 g of 2-O-(5-methyl-3-isoxazolyl)glycerol (prepared as described in Preparation 20), 5.93 ml of dihydropyran and 0.15 g of pyridine p-toluenesulfonate in 110 ml of methylene chloride was stirred at room temperature for 14 hours. The solvent was removed by evaporation under reduced pressure, and then the residue was subjected to column chromatography through 350 g of silica gel. 3.32 g of the 1,3-ditetrahydropyranyl compound was first eluted with a 1:4 by volume mixture of ethyl acetate and hexane, and then 9.67 g of the title compound were isolated as a colorless oil from the fractions eluted with a 1:1 by volume mixture of ethyl acetate and hexane.

Provenance & Evidence