Ethyl chloroacetate → Ethyl 2-nitrothiophene-3-acetate

Participants

Reaction Conditions

Reaction Steps

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].

Provenance & Evidence