Water → HCID 86753079, compound

HRID 2393164Notes

Reaction equation

HRID 2393164 reaction equation
C[C:2]([CH3:5])([O-:4])C.[K+].[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH:17]=O.[OH2:19]>CS(C)=O>[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1/[CH:17]=[CH:17]/[CH2:8][CH2:9][CH2:10][C:11]([O:4][CH2:2][CH3:5])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 796192-QuinolinecarboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 86753079HCID 86753079, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium tert-butoxide (2.14 g) was added gradually to a solution of 2-quinolinecarbaldehyde (2.0 g) and 1-(4-ethoxycarbonyl)butyltriphenylphosphonium bromide (9.0 g) in DMSO (18 ml), and the mixture was stirred at room temperature for 30 minutes. This reaction mixture was poured into iced water and extracted with ether. The ether layer was washed with saturated aqueous sodium chloride solution twice and dried over anhydrous sodium sulfate. The solvent was then distilled off and the crude residue was purified by silica gel column chromatography (hexane-ethyl acetate=10:1) to provide 0.65 g of ethyl (E)-6-(2-quinolyl)-5-hexenoate and 1.45 g of a mixture of (E) and (Z) compounds, both as oil.

Workup

  1. extractionextracted with ether
  2. washThe ether layer was washed with saturated aqueous sodium chloride solution twice
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off
  5. customthe crude residue was purified by silica gel column chromatography (hexane-ethyl acetate=10:1)

Sources & evidence

ORD record
ord-16092cc18b0e418eb9c3e5479b0ac2fd
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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