Water → Ethyl 2-nitrothiophene-3-acetate

Temperature

0 °C

Ethyl thiophene-3-acetate, (10 g, 64.1 mmol) was dissolved in chloroform (90 ml) and trifluoroacetic anhydride (40 ml) at 0° C. Ammonium nitrate (5.2 g, 64.1 mmol) was added and the reaction mixture was stirred at 0° C. for 1 hour then warmed slowly to room temperature for 2 hours. The reaction mixture was cooled in an ice-bath and diluted with dichloromethane (60 ml) and then water (50 ml). The aqueous phase was extracted with dichloromethane and the combined organic fractions were washed with saturated brine solution. The organic phase was dried over magnesium sulfate, evaporated to give a red/brown liquid which was chromatographed on silica gel using hexane/ethyl acetate (4:1) as eluent to give 8.2 g of ethyl 2-nitrothiophene-3-acetate as a red/brown viscous oil.

1. customat 0° C
2. temperaturethen warmed slowly to room temperature for 2 hours
3. temperatureThe reaction mixture was cooled in an ice-bath
4. extractionThe aqueous phase was extracted with dichloromethane
5. washthe combined organic fractions were washed with saturated brine solution
6. dry with materialThe organic phase was dried over magnesium sulfate
7. customevaporated
8. customto give a red/brown liquid which
9. customwas chromatographed on silica gel

ORD record

ord-dfc9f37a2a0640bca6e0e294dbea9d0b

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06528653B2