Ethyl chloroacetate → Ethyl 2-nitrothiophene-3-acetate

Temperature

-50 °C

Potassium tertiary-butoxide (652 mg, 5.81 mmol) was dissolved in tetrahydrofuran (150 ml) and the solution cooled to −50° C. A solution of 2-nitrothiophene (250 mg, 1.94 mmol) (Avocado) and ethyl chloroacetate (0.22 ml, 1.94 mmol) (Aldrich) was added dropwise in dry tetrahydrofuran (4 ml) over 5 minutes. The reaction mixture was stirred at −50° C. for 1 hour then quenched with acetic acid (0.5 ml), then washed with water (20 ml). The aqueous phase was extracted with ethyl acetate and the combined organic fractions were washed with saturated brine solution. The organic phase was dried over magnesium sulfate, evaporated to dryness and the residue chromatographed on silica gel using hexane/ethyl acetate (4:1) as eluent to give 261 mg of ethyl 2-nitrothiophene-3-acetate as a red/brown viscous oil. MS(ES): mn/e 216 [M+H].

1. customthen quenched with acetic acid (0.5 ml)
2. washwashed with water (20 ml)
3. extractionThe aqueous phase was extracted with ethyl acetate
4. washthe combined organic fractions were washed with saturated brine solution
5. dry with materialThe organic phase was dried over magnesium sulfate
6. customevaporated to dryness
7. customthe residue chromatographed on silica gel

ORD record

ord-d9e31310cf89454a9b892991642a3a43

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06528653B2