(Diethylamino)sulfur trifluoride → 2-(p-Octyloxyphenyl)-5-(3-fluoro-6-oxanonyl)pyridine

Participants

Reaction Steps

0.11 mol of DAST is added at -30° C. to a solution of 0.1 mol of 2-(p-octyloxyphenyl)-5-(3-hydroxy-6-oxanonyl)pyridine (obtainable by reaction of 2-(p-octyloxyphenyl)-5-methylpyridine with LDA at -40° C. and optically active 1,2-epoxy-5-oxaoctane) in methylene chloride, and the reaction mixture is then warmed slowly to room temperature. After 12 hours, the mixture is subjected to customary work-up, and the product is purified by crystallization, to give optically active 2-(p-octyloxyphenyl)-5-(3-fluoro-6-oxanonyl)pyridine.

Provenance & Evidence