Tributylvinyltin → HCID 14167864, compound

Participants

Reaction Steps

A mixture of 0.4645 g (0.00073 mole) of diphenylmethyl 7-phenylacetamido-3-trifluoromethylsulfonyloxy-3-cephem4-carboxylate, 0.279 g (0.00088 mole) of ethenyl tri-n-butylstannane, 0.200 g (0.00146 mole) of zinc chloride and 0.0068 g (0.000029 mole) of tri-(2-furyl)phosphine in 6 mL of dry 1-methyl-2-pyrrolidinone, under an Argon atmosphere, was degassed for 30 seconds. Then 0.0084 g (0 000014 mole) of palladium(0) bis(dibenzylidene acetone) was added all at once. The reaction mixture was stirred at room temperature for 1 hr. The reaction mix was then diluted with ethyl acetate and the organic solution washed with dilute ammonium chloride. The ethyl acetate was removed at reduced pressure and replaced with acetonitrile. The organic phase was washed with n-pentane and the acetonitrile removed at reduced pressure. The residue was crystallized from ethanol/methylene chloride yielding 0.320 g (85%) of diphenylmethyl 7-phenylacetamido-3-ethenyl-3-cephem-4-carboxylate. The nuclear magnetic resonance spectrum was consistent for the desired structure.

Provenance & Evidence