Phosphorus oxide (P4O10) → 4H,5H,6H-cyclopenta(b)thiophen-6-one

Participants

Reaction Steps

To a suspension of P2O5 (25.4 g, 179.0 mmol) in methanesulfonic acid (100 mL) was added 3-(thiophen-3-yl)propanoic acid (5.0 g, 32.0 mmol) and the reaction was stirred at room temperature for 1 h. At completion, the reaction was concentrated and the residue was purified by flash chromatography (20-30% EtOAc/hexane eluent) to give 4H-cyclopenta[b]thiophen-6(5H)-one (1.34 g, 30% yield) as a brown solid. 1H NMR (300 MHz, MeOH) δ ppm 8.14 (d, J=4.8 Hz, 1H), 7.17 (d, J=4.8 Hz, 1H), 2.94-3.15 (m, 4H); MS (EI) m/z=139.2 [M+1]+.

Provenance & Evidence