Methyl iodide → 1-(1-Methyl-1H-indol-3-yl)ethanone

HRID 1599462Notes

Reaction equation

HRID 1599462 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:15]I>C1COCC1>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:15])[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 128023-AcetylindoleHCID 24758Sodium hydride

Product 1

HCID 5941561-(1-Methyl-1H-indol-3-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Acetyl-1H-indole (4.00 g, 0.025 mol) was dissolved in dry THF (100 ml), and treated with 80% sodium hydride (0.794 g, 0.0263 mol) with stirring under At. After 0.5 h, methyl iodide (2.36 ml, 0.038 mol) was added. After 20 h, the reaction mixture was evaporated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was then dried (Na2SO4), and evaporated under reduced pressure to give the title compound as a pale brown oil which crystallised on standing (4.20 g, 97%).

Workup

  1. waitAfter 20 h
  2. customthe reaction mixture was evaporated under reduced pressure
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was then dried (Na2SO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-be5f5a6e4fee45278494c79fe8a61391
Source dataset
uspto-grants-1998_04
Patent number
US05741801

Reaction notes

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