Anisole → 3-Phenylthio-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid

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Reaction Steps

A solution of 50 mg of 3-phenylthio-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid diphenylmethyl ester, and 50 mg of anisole in 1 mL of trifluoroacetic acid was stirred for 5 min at room temperature after which time the solvent was removed by evaporation. Trituration of the residue with ether-petroleum ether afforded 26 mg (80%) of 3-phenylthio-6-(1-hydroxyethyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid as colorless crystals. IR (Nujol mull): 1765, 1650, 1535 cm-1 ; NMR (220 MHz; CDCl3 /DMSO-D6): δ 1.18 (3H, d, J=6.5), 2.32 (1H, dd, J=19, 3.5), 2.67 (1H, m), 2.85 (1H, dd, J=19, 8), 3.07 (1H, m), 3.92 (1H, dq, J=6.5, 6.5), 4.41 (1H, m), and 7.3-7.6 (5H, m).

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