3,3-Dimethyl-1,3-dihydro-indol-2-one → 3,3-Dimethylindoline

HRID 2192217Notes

Reaction equation

HRID 2192217 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1([CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=O>C1COCC1>[CH3:7][C:8]1([CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH2:9]1

Participants

4

Reactant 2

HCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 118049123,3-DimethylindolineYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 1M of LAH (30 mL) in THF was added 2b (630 mg, 3.88 mmol) in portion. The reaction mixture was stirred at rt for 2 h, then refluxed for 1 h. The reaction mixture was quench with 1 part of H2O (10 mL), one part of 15% NaOH (5 mL) and another part of H2O (5 mL). The aqueous layer was extracted with EtOAc. The EtOAc layer was dried over Na2SO4 and filtered. The solvent was evaporated under reduced pressure to afford 2c (320 mg, 56%) as an oil. MS (ES) m/z 150 [M+H]+.

Workup

  1. temperaturerefluxed for 1 h
  2. customThe reaction mixture was quench with 1 part of H2O (10 mL), one part of 15% NaOH (5 mL)
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialThe EtOAc layer was dried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b723bc29558e437c8752d67809c0ba51
Source dataset
uspto-grants-2012_12
Patent number
US08329718B2

Reaction notes

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