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

HRID 1680024Notes

Reaction equation

HRID 1680024 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-d3347a73ccd944d1b7f4a8b7d0092f9b
Source dataset
uspto-grants-1981_06
Patent number
US04271170

Reaction notes

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