Ethyl Acetate → HCID 18546255, compound

Participants

Reaction Steps

A solution of (3RS,4RS)-3-ethyl-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-4-(2-propenyl)chroman-2-one (9.4 g) in dry tetrahydrofuran (50 ml) was added dropwise to an ice-cold suspension of lithium aluminum hydride (2.2 g) in dry tetrahydrofuran (50 ml) over 25 minutes under nitrogen atmosphere, and the reaction mixture was then stirred on ice for 1 hour and 15 minutes. Ethyl acetate (30 ml) and saturated aqueous ammonium chloride (30 ml) were added to stop the reaction, followed by stirring for 1 hour at room temperature. The reaction mixture was filtered through cellite and the resulting filtrate was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous ammonium chloride, dried over magnesium sulfate, and then concentrated under reduced pressure to give (2RS,3RS)-2-ethyl-3-(2-hydroxy-4-methoxymethoxyphenyl)-2-(4-methoxymethoxyphenyl)-5-hexenol (9.5 g, quantitative) as a crude product, which was then used for the subsequent reaction without further purification.

Provenance & Evidence