Ammonium Chloride → 2-tert-Butyl-1H-indole

HRID 423745Notes

Reaction equation

HRID 423745 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=O.[Li]CCCC.[NH4+].[Cl-]>C1COCC1>[C:2]([C:3]1[NH:5][C:6]2[C:7]([CH:12]=1)=[CH:8][CH:9]=[CH:10][CH:11]=2)([CH3:14])([CH3:13])[CH3:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27340052,2,2'-TrimethylpropionanilideHCID 178418339Butyllithium

Product 1

HCID 5941662-tert-Butyl-1H-indoleYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of 2,2-dimethyl-N-o-tolyl-propionamide (30.0 g, 159 mmol) in dry THF (100 mL) was added dropwise n-BuLi (2.5 M, in hexane, 190 mL) at 15° C. The mixture was stirred overnight at 15° C., cooled in an ice-water bath and treated with saturated NH4Cl solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography to give 2-tert-butyl-1H-indole (23.8 g, 88%).

Workup

  1. temperaturecooled in an ice-water bath
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a64e3a6956674499ac9d77232b7f7a84
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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