1H-Imidazole-4-carbaldehyde → Triphenylphosphine Oxide

HRID 1446805Notes

Reaction equation

HRID 1446805 reaction equation
[C:1]1([P:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=C(C)C(OC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=C(C=[O:32])N=C1>C(O)C>[C:1]1([P:7](=[O:32])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 764281H-Imidazole-4-carbaldehydeHCID 10569721Methyl 2-(triphenyl-lambda~5~-phosphanylidene)propanoate

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.961 g (10 mmol) of methyl 2-(triphenylphosphoranylidene)propionate [H. J. Bestmann and H. Schulz, Angew. Chem., 73, 27 (1961)] and 3.48 g (10 mmol) of imidazole-4-carboxaldehyde [F. L. Pyman, J. Chem. Soc., 186 (1916)] in 50 ml of absolute ethanol is stirred at room temperature for seven days. At the end of this time, the ethanol is removed in vacuo and the desired product is isolated free of triphenylphosphine oxide by chromatography on silica gel. The product thus obtained is a mixture of E and Z olefin isomers.

Workup

  1. customAt the end of this time, the ethanol is removed in vacuo

Sources & evidence

ORD record
ord-1fc85ae81581434fba6c6d170ce17949
Source dataset
uspto-grants-1982_02
Patent number
US04313948

Reaction notes

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