Acetic Acid → 3-Phenylthio-7-oxobicyclo[3.2.0]heptan-2-carboxylic acid, diphenylmethyl ester

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Reaction Steps

Twenty grams of 7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenylmethyl ester, 13, were dissolved in 40 mL of THF by gentle warming. To this solution at room temperature was added 1.0 mL of triethylamine and 13.0 mL of thiophenol. The resulting solution was stirred under argon at room temperature for 1 hr, after which time 0.5 mL of acetic acid was added, and the solvent was removed by rotary evaporation at 40°. Crystallization from ether at room temperature afforded 21 g (78%) (total of 2 crops) of 3-phenylthio-7-oxobicyclo[3.2.0]heptan-2-carboxylic acid, diphenylmethyl ester, 14. NMR (220 MHz; CDCl3): δ 2.23 (1H, m), 2.43 (1H, m), 2.84 (1H, m), 3.07 (2H, m), 3.41 (1H, m), 3.80 (2H, m), 6.77 (1H, s), and 7.0-7.3 (15H, m).

Provenance & Evidence