Anisole → 3-Phenylthio-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic Acid

Participants

Reaction Steps

A solution of 150 mg of 3-phenylthio-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenylmethyl ester, and 135 mg of anisole in 3 mL of trifluoroacetic acid was stirred at room temperature for 15 min. The solvent was removed with a stream of nitrogen leaving a residual oil which when triturated with ether afforded 77 mg (84%) of colorless crystals of 3-phenylthio-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid. NMR (220 MHz; CDCl3): δ 2.27 (1H, dd, J=17, 3), 2.75 (1H, m), 2.68 (1H, m), 3.0-3.25 (1H, m), 4.50 (1H, m), 7.2-7.4 (3H, m), and 7.4-7.6 (2H, m).

Provenance & Evidence