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

Participants

Reaction Steps

2-Amino-5-phenyl thiophene-3-carboxylic ethyl ester was prepared according to the method described by Hwang et al., 2001. t-Butylnitrite (1.6 mL, 13.3 mmol) and anhydrous copper (II) chloride (25 mmol) were dissolved in IMS (100 mL). To this was added 2-amino-5-phenyl-thiophene-3-carboxylic acid ethyl ester (6.9 mmol) in one portion and the reaction was stirred for 1 hour. The reaction was quenched with saturated aqueous ammonium chloride (2 mL) and the solvent evaporated. The resulting slurry was partitioned between DCM and water. The organic solution was separated and dried over magnesium sulfate, filtered and the solvent evaporated to give the title compound as a brown oil (1.7 g, 98%). 1H NMR (400 MHz, CHCl3-d): δ 8.0 (s, 1H), 7.75 (s, 1H), 7.65 (d, 2H), 7.4 (t, 2H), 7.3 (m, 1H), 4.35 (q, 2H), 1.4 (t, 3H).

Provenance & Evidence