Methyltriphenylphosphonium iodide → HCID 18782830, compound

Participants

Reaction Steps

Methyltriphenylphosphonium iodide (3.17 g, 7.84 mmol) was suspended in anhydrous THF (20 ml) under an atmosphere of dry N2. To this solution was added a 1.0 M solution of potassium tert-butoxide (7.84 ml) in THF. After the reaction has stirred at ambient temperature for 30 min, a solution of 2-acetyl-6,6-dimethyl-bicyclo[3.1.1]heptane-3-carbonitrile (1.00 g, 5.23 mmol), prepared in step A of example 42, dissolved in anhydrous THF (10 ml) was added to the reaction. After stirring for two hours, the reaction was then partitioned between ethyl ether and water. The ethyl ether layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum to give an oil which was chromatographed on silica gel using a gradient of neat hexanes to 10% ethyl acetate in hexanes to give 490 mg of the titled compound as an oil: C.I. m/z 190 [M+1]; 1H NMR (CDCl3)δ 4.82 (m, 2H), 2.82 (m, 2H), 2.10-2.28 (m, 3H), 1.93 (m, 2H), 1.75 (s, 3H), 1.33 (d, J=9.9 Hz, 1H), 1.23 (s, 3H), 0.93 (s, 3H), 0.80-0.87 (m, 2H).

Provenance & Evidence