Sodium Hydroxide → (-)-5-Decyloxy-2-[4-(6-hydroxyheptenyl)phenyl]pyrimidine

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Reaction Steps

In a reactor equipped with a stirrer and a thermometer, 5-decyloxy-2-(4-bromophenyl)pyrimidine (13.98 g), dry tetrahydrofuran (THF) (30 ml), tetrakis(triphenylphosphine)palladium (0.11 g) and sodium hydroxide (1.2 g) are charged. To the mixture, a solution of a reaction product of 6-hydroxy-1-heptyne and catechol borane (5 g) dissolved in THF (12 ml) is dropwise added, followed by heating up to a refluxing temperatur. After reacting for 4 hours, the reaction mixture is cooled to room temperature. To the mixture, toluene and water are added for extraction, and the organic layer is washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. A resulting residue is purified by silica gel column chromatography (eluent: toluene-ethyl acetate) to obtain (-)-5-decyloxy-2-[4-(6-hydroxyheptenyl)phenyl]pyrimidine (7.99 g).

Provenance & Evidence