Water → Ethyl (bicyclo[3.2.0]heptan-6-ylidene)acetate

Participants

Reaction Steps

Triethylphosphonoacetate (96.2 g; 429 mmol) was added to a suspension of 60% sodium hydride dispersion (16.5 g; 413 mmol) in tetrahydrofuran (480 mL) maintaining the temperature between 1–4° C. A solution of bicyclo[3.2.0]heptan-6-one (35.0 g; 318 mmol) in tetrahydrofuran (320 ml) was added maintaining the temperature between 5–15° C. The reaction mixture was stirred at ambient temperature overnight. Demineralised water (350 mL) added and the product was extracted with diethyl ether (3×450 ml). The combined organic phases were washed with brine (300 ml), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to leave a pale orange oil. This was purified by chromatography on a silica pad, eluting with 1:19 ethyl acetate:n-hexane. The product containing fractions were combined and concentrated in vacuo to yield the title compound as a colourless oil (47.8 g).

Provenance & Evidence