Methyl iodide → 1-Methyl-3-phenylindole

HRID 590953

Reaktionsgleichung

Reaktionsgleichung von HRID 590953
[H-].[Na+].[C:3]1([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:18]I>CN(C)C=O>[CH3:18][N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:10]1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 965023-Phenylindole

Produkt 1

HCID 6101761-Methyl-3-phenylindoleAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (60% in mineral oil, 200 mg, 5 mmol) was added at 0° C. to a solution of 3-phenyl-1H-indole (1a) (940 mg, 4.86 mmol) in N,N-dimethylformamide (20 mL) under a nitrogen atmosphere. The suspension was stirred for 15 minutes at 0° C. and methyliodide (311 μL, 5 mmol) was then added. The reaction mixture was warmed to room temperature, stirred for 6 hours and then concentrated in vacuo. The residue was partitioned between ethyl acetate (30 mL) and water (10 mL). The organic layer was washed with water (2×10 mL), brine (10 mL), dried over sodium sulfate, filtered and evaporated to dryness to give the desired product (1b) as a yellow oil (1 g, 4.86 mmol, 100%) which was used without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for 6 hours
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate (30 mL) and water (10 mL)
  5. washThe organic layer was washed with water (2×10 mL), brine (10 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-89d5c2fb175646cda65462c0f32c8520
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238026B2

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