Sodium sulfate decahydrate → 4-({[5'-(hydroxymethyl)-2,2',6-trimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-ol

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Reaction Steps

To a solution of methyl 4′-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6,6′-trimethylbiphenyl-3-carboxylate (191 mg, 0.48 mmol) in anhydrous tetrahydrofuran (3 mL) was added lithium aluminum hydride (34.2 mg, 0.72 mmol) under ice-cooling, and the mixture was stirred overnight at room temperature. Anhydrous tetrahydrofuran (10 mL) was added to the reaction solution, and the solution was ice-cooled. Sodium sulfate decahydrate (232 mg, 0.72 mmol) was added, and the mixture was stirred at room temperature for 2 hr. The precipitated insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure to give the title compound (182 mg, yield 100%) as a colorless amorphous powder.

Provenance & Evidence