Malic Acid → 5-Heptyl-2-(4-(2-fluoro-5-oxaoctyloxy)phenyl)pyrimidine

Participants

Reaction Steps

A solution of 0.1 mol of 5-heptyl-2-(4-2-hydroxy-5-oxaoctyloxy)phenyl)pyrimidine (prepared by heating optically active 1,2-epoxy-5-oxaoctane, obtainable from malic acid, with 5-heptyl-2-(p-hydroxyphenyl)pyrimidine in the presence of dry potassium carbonate and methyl ethyl ketone as solvent) in methyl chloride is cooled to -40° C., and 0.11 mol of DAST is added dropwise with exclusion of moisture. The reaction mixture is subsequently stirred at room temperature for 12 hours with slow warming, then hydrolyzed with ice cooling and washed with dilute sodium hydroxide solution and several times with water. After the mixture has been dried over magnesium sulfate, the solvent is removed on a rotary evaporator, and the crude product is purified by chromatography and crystallization, to give optically active 5-heptyl-2-(4-(2-fluoro-5-oxaoctyloxy)phenyl)pyrimidine, C 41 SA (35) I.

Provenance & Evidence