Methyl iodide → 5-Benzyloxy-1-methylindole-3-carboxaldehyde

HRID 1985425Notes

Reaction equation

HRID 1985425 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH:18]=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:22]I.[Cl-].[NH4+]>CN(C)C=O.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:22])[CH:13]=[C:12]2[CH:18]=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 813985-(phenylmethoxy)-1H-indole-3-carbaldehyde

Product 1

HCID 122838545-Benzyloxy-1-methylindole-3-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5g of 5-Benzyloxyindol-3-aldehyde was dissolved in 50 ml of N,N-dimethylformamide, and 0.84 g of 60% sodium hydride was added under ice-cooling. The reaction solution was stirred at room temperature for 30 minutes, 2.5 ml of methyl iodide was added and stirring was continued at room temperature for 16 hours. The reaction solution was cooled with ice, treated with water and ammonium chloride, and extracted with ethyl acetate and tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was treated with diethyl ether and filtered, to give 4.6 g of the title compound.

Workup

  1. temperaturecooling
  2. stirringstirring
  3. waitwas continued at room temperature for 16 hours
  4. temperatureThe reaction solution was cooled with ice
  5. extractionextracted with ethyl acetate and tetrahydrofuran
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. additionThe residue was treated with diethyl ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-bd079e0cfbdd467fb15f39e2bfe8729b
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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