Water → HCID 68107165, compound

Participants

Reaction Steps

A solution of 4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-ol (0.680 g, 3.27 mmol) in dichloromethane (16.0 mL) was cooled to −78° C., and titanium tetrachloride (0.720 mL, 6.53 mmol) was added dropwise thereto. After stirring the mixture for 1 hour, 1.0 mol/L dimethylzinc solution in n-hexane (13.1 mL, 13.1 mmol) was added dropwise thereto. The mixture was stirred for 2 hours, and water was added to stop the reaction. The temperature was returned to room temperature, and the mixture was diluted with ethyl acetate and 1 mol/L hydrochloric acid. The organic layer was washed with water and then with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure, and the obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=90/10-30/70) to obtain 0.641 g of the captioned compound (95% yield).

Provenance & Evidence