Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl-(E)-3-(1-methyl-1,2,3-triazol-4-yl)acrylate

HRID 376460Notes

Reaction equation

HRID 376460 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=O)[N:4]=[N:3]1.[CH3:9][O:10][C:11]([CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:12]>ClCCl>[CH3:9][O:10][C:11](=[O:12])/[CH:13]=[CH:7]/[C:5]1[N:4]=[N:3][N:2]([CH3:1])[CH:6]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 143134381-Methyl-1H-1,2,3-triazole-4-carboxaldehyde

Product 1

HCID 21202730Methyl-(E)-3-(1-methyl-1,2,3-triazol-4-yl)acrylateYield 212.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Methyl-1,2,3-triazol-4-carboxaldehyde (1 g, 9 mmol) was added to a solution of methoxycarbonylmethylene triphenylphosphorane (4.5 g, 13.5 mmol) in dichloromethane (50 ml) and stirred at room temperature for 3.5 hours. The solvent was removed and the residue purified by silica gel chromatography to afford the title compound, (3.2 g).

Workup

  1. customThe solvent was removed
  2. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-306f5d0ea46a40ce95e15948c0726ac3
Source dataset
uspto-grants-2000_02
Patent number
US06020368

Reaction notes

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