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

HRID 362791Notes

Reaction equation

HRID 362791 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 Ar. 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-91a523413b884541b67862091b944cc1
Source dataset
uspto-grants-1999_02
Patent number
US05872134

Reaction notes

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