Sodium sulfate decahydrate → (4-{1-[(4-Phenyl-1,3-thiazol-2-yl)methyl]butyl}phenyl)methanol

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Reaction Steps

To a suspension of triphenyl[(4-phenyl-1,3-thiazol-2-yl)methyl]phosphonium bromide (1.00 g, 1.94 mmol) synthesized according to the method described in Liebigs Annalen der Chemie, 1981, vol. 4, pp. 623-632 and benzene (20 mL) was added potassium tert-butoxide (239 mg, 2.13 mmol), and the mixture was stirred under an argon atmosphere at room temperature for 3 hr. A solution of methyl 4-butyrylbenzoate (319 mg, 1.55 mmol) in benzene (20 mL) was added dropwise to the reaction solution, and the mixture was stirred at room temperature for 3 hr, and further heated under reflux for 16 hr. The reaction mixture was allowed to cool to room temperature, poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-20:80) to give a yellow oil. A mixture of the obtained oil, tetrahydrofuran (20 mL), methanol (10 mL) and 10% palladium-carbon (50% water-containing product, 200 mg) was stirred under a hydrogen atmosphere at room temperature for 2 days. The catalyst was filtered off, and the obtained filtrate was concentrated to give a colorless oil. To a solution of the obtained oil in tetrahydrofuran (10 mL) was added dropwise 1.0 M diisobutylaluminum hydride toluene solution (10 mL, 10 mmol) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hr, sodium sulfate decahydrate was added and the mixture was further stirred at room temperature for 1 hr. The insoluble material was filtered off, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90-60/40) to give the title compound (250 mg, yield 48%) as a colorless oil.

Provenance & Evidence