Acetic Acid → HCID 178468652, compound

Participants

Reaction Steps

To a solution of 0.10 g (0.49 mmol) of the above-prepared 1-(2-phenyl-thiazol-5-yl)-ethanone was added 0.11 g (0.98 mmol) of 1M potassium tert-butoxide in tetrahydrofuran. The solution was allowed to stir for 0.5 hours. 0.15 g (0.98 mmol) of diethyl oxalate was added and the solution was allowed to stir for 2 hours. The reaction was quenched with aqueous ammonium chloride and partitioned with ethyl acetate. The organic phase was twice washed with aqueous ammonium chloride, once with water, once with brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was dissolved in ethanol (10 ml). To the ethanolic solution was added 0.04 g (0.64 mmol)of glacial acetic acid followed by 0.03 g (0.64 mmol) of hydrazine monohydrate. The solution was allowed to stir for 3 hours at room temperature. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using 9:1 hexanes:ethyl acetate as eluant to give 75 mg of the title compound (51%). 1H NMR (500 MHz, CDCl3) δ 8.10 (s, 1H) 7.98 (m, 2H) 7.47 (m, 3H) 7.10 (s, 1H) 4.42 (q, 2H) 1.42 (t, 3H).

Provenance & Evidence