Acetic Acid → HCID 69663723, compound

Temperature

-10 °C

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).

1. concentrationIt was concentrated under reduced pressure
2. additionTo the residue were added water
3. extractiona 1N aqueous solution of sodium hydroxide, and the mixture was extracted with ethyl acetate
4. washThe oily phase was washed with saturated aqueous ammonia and brine in turn
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by column chromatography on silica gel

ORD record

ord-6361be8b57954c7786f38435bff51d8a

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07022732B2