Triphenylphosphine → (2R,5R)-(4'-octyloxy-3'-cyanobenzoyloxy)-5-hexyl-delta-valerolactone

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Reaction Steps

In 1 ml of dehydrated benzene were suspended 100 mg of (2S,5R)-2-hydroxy-5-hexyl-δ-valerolactone synthesized in the same manner as described in Referential Example 2 and 120 mg of 4-octyloxy-3-cyanobenzoic acid, and 0.1 ml of diethyl azodicarboxylate was added to the suspension with stirring at room temperature. Then, 150 mg of triphenylphosphine was added to the mixture and reaction was carried out overnight with stirring. The reaction mixture was concentrated under a reduced pressure and the residue was separated and purified by the silica gel column chromatography using an n-hexane/benzene (1/4) mixed solvent as the developing solvent. Recrystallization from ethanol gave 90 mg of (2R,5R)-(4'-octyloxy-3'-cyanobenzoyloxy)-5-hexyl-δ-valerolactone. When the phase transition behavior of the obtained compound was measured by a differential thermal scanning calorimeter and a polarization microscope, the following results were obtained: ##STR88##

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