Water → HCID 18546260, compound

Participants

Reaction Steps

A 40% solution of diethyl azodicarboxylate in toluene (21.9 ml) was added dropwise to an ice-cold solution of (2RS,3RS)-2-ethyl-3-(2-hydroxy-4-methoxymethoxyphenyl)-2-(4-methoxymethoxy-phenyl)-5-hexenol (9.5 g) and triphenylphosphine (15.0 g) in dry 1,4-dioxane (150 ml) over 25 minutes under nitrogen atmosphere. The reaction mixture was stirred for 10 minutes on ice and for 30 minutes at room temperature. Under ice-cooling, water was added to the reaction mixture, which was then extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulfate and then concentrated to give a crude product, which was then purified by flash column chromatography (silica gel: Merck Kieselgel 60, eluent: hexane/ethyl acetate=50/1→20/1→10/1) to give (3RS,4RS)-3-ethyl-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-4-(2-propenyl)chroman (8.4 g, Yield 92.6%) as a white solid.

Provenance & Evidence