Tert-Butyl nitrite → Ethyl 5-phenylthiophene-3-carboxylate

Participants

Reaction Steps

Anhydrous copper (II) chloride (4 g, 0.03 mol) and tert-butyl nitrite (1.9 mL, 0.019 mol) were dissolved in IMS (100 mL) then treated with 2-amino-5-phenyl-thiophene-3-carboxylic acid ethyl ester (2 g, 8.097 mmol). After 30 minutes saturated aqueous ammonium chloride (20 mL) was added and the mixture left for a further 30 minutes. The resultant precipitate was filtered off and the filtrate was concentrated, washed with DCM, dried and concentrated to give a dark oil which was purified by column chromatography, eluting with 0-35% tert-butyl methyl ether in cyclohexane to afford 5-phenyl-thiophene-3-carboxylic acid ethyl ester as a yellow oil (1.38 g).

Provenance & Evidence