Chloromethyl Methyl Ether → N-(methoxymethyl)-3-indolecarboxaldehyde

HRID 1985418Notes

Reaction equation

HRID 1985418 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[H-].[Na+].[CH3:14][O:15][CH2:16]Cl.[Cl-].[NH4+]>CN(C)C=O.O>[CH3:14][O:15][CH2:16][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1

Participants

7

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 11137907N-(methoxymethyl)-3-indolecarboxaldehydeYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5 g of Indol-3-aldehyde was dissolved in 40 ml of N,N-dimethylformamide, and 1.38 g of 60% sodium hydride was added under ice-cooling. The reaction solution was stirred for 20 minutes with ice-cooling, then 3.2 ml of chloromethyl methyl ether was added, and stirring was continued at room temperature for 16 hours. The reaction solution was cooled in ice, treated with water and ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was subjected to silica gel column chromatography, to give 6.1 g of the title compound (20-44% ethyl acetate-hexane)

Workup

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

Sources & evidence

ORD record
ord-f5c1de5088d541d78e883ad691615c2e
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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