Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 3-(6-Methylpyridin-2-yl)acrylic acid ethyl ester

HRID 1716771Notes

Reaction equation

HRID 1716771 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[C:10]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:12][CH2:13][CH3:14])=[O:11]>C1(C)C=CC=CC=1>[CH2:13]([O:12][C:10](=[O:11])[CH:15]=[CH:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)[CH3:14]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 707376-Methyl-2-pyridinecarboxaldehyde

Product 1

HCID 673561473-(6-Methylpyridin-2-yl)acrylic acid ethyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6-methyl-pyridine-2-carbaldehyde (3.0 g, 24.8 mmol) and carbethoxymethylene triphenylphosphorane (9.5 g, 27.2 mmol) in toluene (20 ml) was stirred at room temperature overnight. The precipitate was filtered and washed with toluene. The filtrate was concentrated, and the residue was purified via flash chromatography (DCM/MeOH) affording 3-(6-Methyl-pyridin-2-yl)-acrylic acid ethyl ester CCLII in 63% yield (2.95 g).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with toluene
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified via flash chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-322954ded03349409420fb6bb3f59c4e
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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