Sodium Methoxide → HCID 22922141, compound

HRID 2258512Notes

Reaction equation

HRID 2258512 reaction equation
[CH:1]([C:3]1[CH:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][C:4]=1[O:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)=O.C[O-].[Na+]>CO>[CH:21]([C:19]1[CH:18]=[CH:17][C:4]2[O:5][C:6]([C:7]3[CH:16]=[CH:15][C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[N:8]=3)=[CH:1][C:3]=2[CH:20]=1)=[O:22]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 22922159HCID 22922159, compound

Product 1

HCID 22922141HCID 22922141, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(2,4-diformylphenoxymethyl)quinoline (164.6 mg) and sodium methoxide (140 mg) in methanol (10.5 ml) was stirred under reflux for 30 minutes. The reaction mixture was concentrated under reduced pressure, and to the residue was added water and chloroform. The separated organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a crude residue. The residue was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and n-hexane (1:10). The fractions containing object compound were combined and concentrated under reduced pressure to give 2-(5-formylbenzofuran-2-yl)quinoline (31 mg).

Workup

  1. temperatureunder reflux for 30 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionto the residue was added water and chloroform
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a crude residue
  8. washeluted with a mixture of ethyl acetate and n-hexane (1:10)
  9. additionThe fractions containing object compound
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5863be35b7ea46839fd4d64f14a39837
Source dataset
uspto-grants-1997_08
Patent number
US05661159

Reaction notes

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