3-Cyclopentyloxy-4-methoxybenzaldehyde → alpha-(3-Cyclopentyloxy-4-methoxyphenyl)benzylalcohol

Participants

Reaction Conditions

Reaction Steps

Phenyllithium (1.8M solution in cyclohexane/diethyl ether, 25.5 milliliters, 46 mmol) was added dropwise over 15 minutes to a stirred solution of 3-cyclopentyloxy-4-methoxybenz-aldehyde (6 grams, 27 mmol) in dry tetrahydrofuran (20 milliliters) at -78° C. The resulting solution was stirred at -78° C. for 30 minutes and quenched at -78° C. by the rapid addition of aqueous saturated NH4Cl (70 milliliters). After warming to room temperature, water was added to dissolve the solids and volatiles were removed in vacuo. The residue was partitioned between water (250 milliliters) and ethyl acetate (250 milliliters), the aqueous phase was extracted with ethyl acetate (3×250 milliliters) and the combined organic layers washed with water (200 milliliters). The organics were dried over Na2SO4 and concentrated in vacuo to give a light yellow oil. The oil was purified by flash chromatography (SiO2 :hexane/ethyl acetate (4:1)) to afford the title compound as a pale yellow oil (7.4 grams) .

Provenance & Evidence