Sodium hydride → Ethyl 4-chloro-6-(4-formylphenoxy)-1-methyl-2-indolecarboxylate

HRID 565050Notes

Reaction equation

HRID 565050 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12].[H-].[Na+].F[C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:21]2[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 21194263Ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate

Product 1

HCID 21194191Ethyl 4-chloro-6-(4-formylphenoxy)-1-methyl-2-indolecarboxylateYield 64.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 1.00 g (3.94 mmol) of ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate was added to a suspension of 0.16 g (3.94 mmol) of 60% sodium hydride and 30 ml of dimethylformamide, the suspension was stirred at room temperature until the mixture became an almost transparent solution. Then 0.54 g (4.34 mmol) of 4-fluoro-benzaldehyde was added to the solution at room temperature followed by stirring for 10 hours at 70° C. The reaction mixture was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate. The combined extracts were washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was isolated and purified by silica gel column chromatography to give 0.91 g (64.5%) of ethyl 4-chloro-6-(4-formylphenoxy)-1-methyl-2-indolecarboxylate.

Workup

  1. stirringby stirring for 10 hours at 70° C
  2. additionThe reaction mixture was poured onto ice water
  3. extractionThe resulting mixture was then extracted three times with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was isolated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-ea34c92f357e4de4896c01461489c2e5
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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