Methanol → HCID 18957483, compound

Participants

Reaction Conditions

Reaction Steps

To a solution 3-(3-Cyclopentyloxy-4-methoxyphenyl)cyclopent-2-en-1-one (275 mg, 1.01 mmol) (E7) in benzene (5 ml) at 0° C. under an argon atmosphere was added a toluene solution of diisobutylaluminum hydride (1M, 1.5 ml, 1.5 mmol) and the resulting mixture was stirred at 0° C. for 1 hr. The mixture was treated with methanol (5 ml) , poured into ether (100 ml) , filtered and concentrated under reduced pressure. The crude product was combined with the product to a similar reaction conducted on 55 mg of ketone and was purified by flash chromatography, eluting with 5:3.5:1 hexanes/ether/methylene chloride to provide a solid. Recrystallization from hexanes/ether provided the title compound (92 mg, 27.7%): m.p. 105°-107° C.; an additional 150 mg was recovered from the mother liquor.

Provenance & Evidence