Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E)-3-[4-(3-Pyridylmethyl)phenyl]acrylic acid methyl ester

HRID 2296045Notes

Reaction equation

HRID 2296045 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)[CH:2]=1.[CH3:16][O:17][C:18]([CH:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:19]>C(Cl)(Cl)Cl>[CH3:16][O:17][C:18](=[O:19])/[CH:20]=[CH:12]/[C:11]1[CH:14]=[CH:15][C:8]([CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 128821774-(3-Pyridylmethyl)benzaldehyde

Product 1

HCID 12882181(E)-3-[4-(3-Pyridylmethyl)phenyl]acrylic acid methyl esterYield 45.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 200 mg of 4-(3-pyridylmethyl)benzaldehyde (prepared as described in Reference Example 1), 0.14 g of methoxycarbonylmethylenetriphenylphosphorane and 5 ml of chloroform was stirred at room temperature for 3 days, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride as eluent to give 48 mg of the title compound having the following physical characteristics:

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-12d0e5a5b1e342ec95620ceef573372a
Source dataset
uspto-grants-1984_01
Patent number
US04427682

Reaction notes

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