Triethyl phosphonoacetate → Ethyl 3-(4-nitrophenyl)-3-phenylprop-2-enoate

HRID 66615Notes

Reaction equation

HRID 66615 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([CH2:8]P(=O)(OCC)OCC)=[O:7])[CH3:4].[N+:17]([C:20]1[CH:33]=[CH:32][C:23]([C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=O)=[CH:22][CH:21]=1)([O-:19])=[O:18]>COCCOC>[C:26]1([C:24]([C:23]2[CH:32]=[CH:33][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=2)=[CH:8][C:6]([O:5][CH2:3][CH3:4])=[O:7])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 70839Methanone, (4-nitrophenyl)phenyl-

Product 1

HCID 308955Ethyl 3-(4-nitrophenyl)-3-phenylprop-2-enoate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirred suspension of sodium hydride, derived from 10.56 g. of a 50% suspension in mineral oil, in 400 ml. of 1,2-dimethoxyethane was added 51.6 g. of diethyl ethoxycarbonylmethylphosphonate, during 1 hour. When gas evolution ceased, a solution of 47.7 g. of 4-nitrobenzophenone in 400 ml. of 1,2-dimethoxyethane was added, dropwise, during 1.5 hours. Stirring was continued overnight and then the solvent was removed by evaporation in vacuo. The residue was partitioned between ethyl acetate and water. The layers were separated, and the water layer was extracted with fresh ethyl acetate. The combined ethyl acetate solutions were evaporated in vacuo to give the title compound as an oil, which slowly solidified.

Workup

  1. waitwas continued overnight
  2. customthe solvent was removed by evaporation in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe layers were separated
  5. extractionthe water layer was extracted with fresh ethyl acetate
  6. customThe combined ethyl acetate solutions were evaporated in vacuo

Sources & evidence

ORD record
ord-c2861430d7a84f4e9e63be0ff61640c3
Source dataset
uspto-grants-1982_08
Patent number
US04342781

Reaction notes

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