Ethyl Acetate → HCID 18546297, compound

Participants

Reaction Steps

A solution of (3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-(2-propenyl)chroman-2-one (6.91 g) in anhydrous tetrahydrofuran (26 ml) was added dropwise to an ice-cold suspension of lithium aluminum hydride (1.65 g) in anhydrous tetrahydrofuran (50 ml) over 20 minutes under nitrogen atmosphere, and the reaction mixture was then stirred on ice for 50 minutes. Ethyl acetate (20 ml) and saturated aqueous ammonium chloride (20 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)-3-(2-hydroxy-4-methoxymethoxyphenyl)-2-(4-methoxymethoxyphenyl)-2-methyl-5-hexen-1-ol (6.94 g, Yield 99.4%) as a crude product, which was then used for the subsequent reaction without further purification.

Provenance & Evidence