Reaction #93024

Reaction equation

benzhydryl 7-phenylacetamido-3-formyl-2-cephem-4-carboxylate

triphenylphosphine

carbon tetrachloride

ethyl acetate

→

benzhydryl 7-phenylacetamido-3-(2,2-dichlorovinyl)-2-cephem-4-carboxylate

Solvents

N,N-dimethylacetamide

Conditions

Workup

1. 1
   TemperatureAfter being cooled
2. 2
   Otherthe resulting precipitates
3. 3
   Filtrationwere filtered off
4. 4
   Otherthe filtrate was evaporated in vacuo
5. 5
   OtherThe residue was purified by column chromatography on silica gel

Procedure

Zinc powder (78.4 g) was added to a solution of benzhydryl 7-phenylacetamido-3-formyl-2-cephem-4-carboxylate (102.4 g) and triphenylphosphine (367.2 g) in a mixture of carbon tetrachloride (800 ml) and N,N-dimethylacetamide (200 ml) at ambient temperature and the mixture was stirred at 60° C. for 30 minutes. After being cooled, the mixture was added to ethyl acetate (20 l) and the resulting precipitates were filtered off and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel to give benzhydryl 7-phenylacetamido-3-(2,2-dichlorovinyl)-2-cephem-4-carboxylate (15.26 g).

Source