Benzyl Bromide → 1h-Indole,2-ethyl-4-nitro-1-(phenylmethyl)-

HRID 3386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 3386
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:7][CH:6]=2)[CH3:2].[H-].[Na+].CCCCCC.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.O>[C:24]1([CH2:23][N:4]2[C:5]3[C:10](=[C:9]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:7][CH:6]=3)[CH:11]=[C:3]2[CH2:1][CH3:2])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

7

Edukt 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 24758Sodium hydrideHCID 130479942-ethyl-4-nitro-1H-indole

Produkt 1

HCID 105407101h-Indole,2-ethyl-4-nitro-1-(phenylmethyl)-Ausbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

2-Ethyl-4-nitro-1H-indole (4.75 g, 25 mmol) was added to a mixture of 1.0 g (25 mmol) of 60% NaH/mineral oil (washed with hexane before adding DMF) in 40 ml DMF. After 45 minutes, 3.0 ml (25 mmol) of benzyl bromide was added. The mixture was stirred at room temperature for four hours, diluted with water, and extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 20% EtOAc/Hexane to give 6.36 g (91%) of 1-Phenylmethyl-2-ethyl-4-nitro-1H-indole as an oil.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe EtOAc solution was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with 20% EtOAc/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-bbf8230acb4c4efbbe2e5b95721c489b
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733923

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