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

HRID 268889Notes

Reaction equation

HRID 268889 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-carbaldeyde (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-1965383ad4ea457c8c30adb4c6e8a94f
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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