Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 23295685, compound

HRID 1953997Notes

Reaction equation

HRID 1953997 reaction equation
[C:1]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(OCC)=[O:2].[Cl:26][C:27]1[C:32]([O:33][C:34]2[N:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[CH:31][C:30]([NH:40][N:41]=[CH:42][C:43](=O)[C:44]([F:47])([F:46])[F:45])=[C:29]([F:49])[CH:28]=1>C1(C)C=CC=CC=1>[Cl:26][C:27]1[C:32]([O:33][C:34]2[N:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[CH:31][C:30]([N:40]2[C:1](=[O:2])[CH:6]=[C:43]([C:44]([F:47])([F:46])[F:45])[CH:42]=[N:41]2)=[C:29]([F:49])[CH:28]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 70231894HCID 70231894, compound

Product 1

HCID 23295685HCID 23295685, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Carboethoxymethylenetriphenylphosphorane (0.235 g) was added to a suspension of 3,3,3-trifluoro-2-oxopropanal 4-chloro-2-fluoro-5-(pyrimidyloxy)-phenylhydrazone (0.122 g) in toluene (15.0 ml) and the mixture was heated at reflux for 1 hour. The solvent was removed under reduced pressure and the residue chromatographed on silica gel to give the titled compound (0.10 g) mp=156-60° C. 1H NMR (CDCl3, TMS): 7.11(1H, br t), 7.32(1H, m), 7.42(1H, d, J=6.9 Hz), 7.43(1H, d J=9.0 Hz), 8.05(1H, br d), 8.58(2H, br d).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customThe solvent was removed under reduced pressure
  4. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-87e20ebcb4f94fc4822f1dbc4a5b70fc
Source dataset
uspto-grants-2000_09
Patent number
US06121201

Reaction notes

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