Phosphorus oxychloride → HCID 67536680, compound

Participants

Reaction Steps

3a,6a-Dihydro-thieno[3,2-b]thiophene-2-carboxylic acid amide 2 (4.0 g, 21.6 mmol) was mixed with 50 mL of POCl3 and the mixture was heated to reflux for 2 hours before POCl3 was removed with a rotary evaporator. Dichloromethane (100 mL) was added and then 100 mL of ice water was added dropwise. The organic layer was further washed with water (30 mL) twice before the solvent was removed. The brown oil obtained was passed through a short column of silica gel with dichloromethane as eluent. After removal of the solvent, a yellow oil was obtained (2.4 g, yield 67%). 1H NMR (CDCl3, 500 MHz): δ 7.80 (s, 1H), 7.72 (d, 1H, J=5.0), 7.30 (d, 1H, J=5.0); 13C NMR (CDCl3, 500 MHz): δ 143.39, 138.27, 133.52, 129.72, 119.38, 114.60, 110.27.

Provenance & Evidence