Triphenylphosphine → 2-(4-[(E)-hex-2-enyloxy]phenyl)-5-pentyl-1,3,4-thiadiazole

Participants

Reaction Steps

Triphenylphosphine (0.95 g) is added in small portions to a solution of (E)-hex-2-en-1-ol (0.40 g), 2-(4-hydroxyphenyl)-5-pentyl-1,3,4-thiadiazole (0.71 g), diethylazodicarboxylate (0.63 g) in dry tetrahydrofuran (40 cm3) at 0° C. under an atmosphere of nitrogen. The reaction mixture is stirred at room temperature overnight. The solvent is removed under reduced pressure and the crude product was purified by column chromatography on silica gel using a 4:1 petroleum (40-60° C.) ether/ethyl acetate mixture as eluent, followed by recrystallisation from ethanol to yield 0.19 g of 2-(4-[(E)-hex-2-enyloxy]phenyl)-5-pentyl-1,3,4-thiadiazole.

Provenance & Evidence