Water → methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoate

HRID 2287589Notes

Reaction equation

HRID 2287589 reaction equation
[OH-].[Na+].[Br-].[CH3:4][O:5][C:6]([C:8]1[CH:33]=[CH:32][C:11]([CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:10][CH:9]=1)=[O:7].[N:34]1[CH:39]=[CH:38][C:37]([CH:40]=O)=[CH:36][CH:35]=1.O>CS(C)=O>[N:34]1[CH:39]=[CH:38][C:37](/[CH:40]=[CH:12]/[C:11]2[CH:10]=[CH:9][C:8]([C:6]([O:5][CH3:4])=[O:7])=[CH:33][CH:32]=2)=[CH:36][CH:35]=1.[N:34]1[CH:39]=[CH:38][C:37](/[CH:40]=[CH:12]\[C:11]2[CH:10]=[CH:9][C:8]([C:6]([O:5][CH3:4])=[O:7])=[CH:33][CH:32]=2)=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 962WaterHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide

Product 2

HCID 12006312methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoateHCID 70244616methyl 4-[(Z)-2-(4-pyridyl)vinyl]benzoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of sodium hydroxide (830 mg) in dimethylsulfoxide (100 ml) was added (4-methoxycarbonylbenzyl)triphenylphosphonium bromide (10.0 g), and after 30 minutes, 4-pyridinecarbaldehyde (2.22 g) was added thereto under ice-cooling. The mixture was stirred overnight. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (n-hexane-ethyl acetate) to give methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoate (1.18 g) and methyl 4-[(Z)-2-(4-pyridyl)vinyl]benzoate (2.67 g).

Workup

  1. temperatureunder ice-cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-abef8aa73e2f454a9622905a424bdbc2
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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