Toluene → HCID 22841014, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.037 g of dl-cis-2-benzyloxymethyltetrahydropyran-3-ol (prepared as described in Preparation 33), 1.709 g of hexadecyl bromide, 0.77 g of potassium hydroxide and 15 ml of toluene was heated, with stirring, at 120° C. for 10 hours. At the end of this time, the reaction mixture was cooled and then poured into water. The aqueous layer was extracted twice with diethyl ether. The organic layer and the extracts were combined, washed with water, dried over anhydrous magnesium sulfate and condensed by evaporation under reduced pressure. The resulting oily residue (3.3 g) was subjected to column chromatography through 50 g of silica gel. The fraction eluted with a 1:10 by volume mixture of diethyl ether and hexane gave 1.455 g of the title compound as a colorless oily substance.

Provenance & Evidence