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

HRID 1952724Notes

Reaction equation

HRID 1952724 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-5289338f8f8d4baca79632ba92c4e035
Source dataset
uspto-grants-2000_09
Patent number
US06114329

Reaction notes

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