Acetone → HCID 131733503, compound

Participants

Reaction Conditions

Reaction Steps

(3R,4R)-4-((3′-Formyl-2,6-dimethylbiphenyl-4-yl)oxy)tetrahydrofuran-3-yl acetate 13c (280 mg, 0.79 mmol) was dissolved in 5 mL of methanol. The reaction mixture was cooled down to 0° C., followed by addition of sodium borohydride (45 mg, 1.20 mmol), then warmed up to room temperature and stirred for 30 minutes. The resulting mixture was mixed with 5 mL of acetone, and concentrated under reduced pressure. The residue was mixed with 10 mL of water, separated, and the aqueous phase was extracted with ethyl acetate (20 mL×3). The combined organic phase was washed with saturated sodium chloride solution (10 mL×3), dried with anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography with elution system B to obtain the title compound (3R,4R)/(3S,4S)-4-((3′-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl)oxy)tetrahydrofuran-3-yl acetate 13d (200 mg, yield 70.9%) as a colorless slime.

Provenance & Evidence