Benzaldehyde → (2R,3R)-3-benzyloxy-2-butyloctanoic acid

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Reaction Steps

The (2R,3R)-2-butyl-3-hydroxyoctanoic acid t-butyl ester (1.00 g, 3.67 mmol) obtained in Production Example C-1 was dissolved in anhydrous dichloromethane (12 ml). Triethylamine (1.37 g, 13.6 mmol) and trimethylchlorosilane (1.20 g, 11.0 mmol) were added to this solution, which was stirred for 30 minutes at room temperature. Then, distilled water was added thereto, and extracted 3 times with dichloromethane. The resulting organic layer was dried with anhydrous magnesium sulfate, filtered, and condensed. The crude product was dissolved in anhydrous dichloromethane (69 ml), and then cooled to −48° C. Benzaldehyde (584 mg, 5.51 mmol), triethylsilane (641 mg, 5.51 mmol), and trimethylsilyl triflate (408 mg, 1.84 mmol) were sequentially added thereto; the mixture was stirred at −48° C. for 15 minutes, and then warmed to room temperature. After the reaction of 2 hours, an aqueous saturated sodium hydrogen solution was added thereto to be washed. The resulting organic layer was dried with anhydrous magnesium sulfate, filtered, and condensed. The obtained residue was purified by column chromatography (silica gel: 30 g, n-hexane/ethyl acetate=7/1) to produce the target compound (781 mg, 70%).

Provenance & Evidence