1-(Triphenylphosphoranylidene)acetone → HCID 70616394, compound

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A solution of diphenylmethyl 3-formyl-7β-(2-thienylacetamido)ceph-2-em-4-carboxylate (116 mg.) in benzene (3 ml.) was treated with a solution of methylcarbonylmethylenetriphenylphosphorane (150 mg.) in benzene (4 ml.) and the mixture refluxed for 5.75 hours. The organic solution was washed with 2-N-hydrochloric acid and water, dried and evaporated in vacuo. The residual gum (186 mg.) was purified by preparative T.L.C. (Kieselgel HF254+366, developed five times with benzene-ethyl acetate = 8:1) to give the title compound (32 mg, 27%) as a gum, λmax. (CHCl3) 318 nm. (qualitative, τ (CDCl3) 3.00 and 3.86 (CH=CH, two d, J 16 Hz), 3.12 (CHPh2), 3.27 (C(2) -H, broad s), 4.47 (C(7) -H), dd, J 8 and 4 Hz), 4.73 (C(6) -H, d, J 4 Hz), 4.69 (C(4) -H, broad s), 6.16 (CH 2 CONH) and 7.91 (COCH3).

Provenance & Evidence