Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 54370741, compound

HRID 1017994Notes

Reaction equation

HRID 1017994 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]=O)=[N:8][CH:9]=1)([O-:3])=[O:2].[C:12]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13]>C1(C)C=CC=CC=1>[CH2:15]([O:14][C:12](=[O:13])[CH:17]=[CH:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1)[CH3:16]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 151455015-Nitropyridine-2-carbaldehyde

Product 1

HCID 54370741HCID 54370741, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-nitro-2-pyridinecarbaldehyde (2.85 g prepared according the procedure described in J. Med. Chem. 1992, 35, 3675) and (carbethoxymethylene)triphenylphosphorane (6.0 g) in dry toluene (120 ml) under nitrogen was stirred and heated at reflux for 6 hours. After standing at room temperature overnight the reaction mixture was evaporated. The residue was subjected to flash chromatography on silica gel eluting with dichloromethane to give the title compound (0.8 g) as a yellow solid.

Workup

  1. customprepared
  2. temperatureheated
  3. temperatureat reflux for 6 hours
  4. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-c3dae748d3bf43a6b4d078efe8ca413c
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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