Acetic Acid → HCID 69663723, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(2-nitrovinyl)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid ethyl ester (3.7 mmol) in dioxane (10 mL) and ethanol (10 mL) was added dropwise a suspension of NaBH4 (140 mg) in dioxane (4 mL) and ethanol (4 mL) under cooling to −10° C. This solution was stirred at −5° C. for 1 hour and then acetic acid was added. It was concentrated under reduced pressure. To the residue were added water and a 1N aqueous solution of sodium hydroxide, and the mixture was extracted with ethyl acetate. The oily phase was washed with saturated aqueous ammonia and brine in turn, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel and the title compound (790 mg) was obtained from the effluent with hexane/ethyl acetate=30/10 (v/v).

Provenance & Evidence