Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 131717466, compound

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Reaction Steps

A solution of 0.22 g (0.69 mmol) of the resultant compound of Example 32 in 15 ml of dichloromethane was cooled to -78° C. and treated with a stream of O3 in air until the blue color persisted. The solution was subsequently purged with air until the blue color was discharged, treated with 0.5 ml of dimethylsulfide, allowed to warm to ambient temperature over 40 min, and treated with 0.29 g (0.87 mmol) of methyl (triphenylphosphoranylidene)acetate. The resulting solution was stirred at ambient temperature for 4 h, concentrated in vacuo, partitioned between dichloromethane and water, dried over MgSO4, and concentrated. Silica gel chromatography using 30% ethyl acetate in hexane provided 0.08 g (31%) of the desired compound (Rf 0.17, 30% ethyl acetate in hexane). 1H NMR (CDCl3) δ 0.89 (d, J=7 Hz, 3 H), 0.93 (d, J=7 Hz, 3 H), 1.22 (m, 2 H), 1.44 (s, 9 H), 1.69 (m, 1 H), 3.06 (s, 3 H), 3.78 (s, 3 H), 3.92 (m, 1 H), 4.58 (br d, 1 H), 5.40 (m, 1 H), 6.16 (dd, J=15, 2 Hz, 1 H), 6.87 (dd, J=15, 6 Hz, 1 H). Mass spectrum: (M+H)+ =380.

Provenance & Evidence