Water → 5-Fluoro-3,3-dimethylindoline

HRID 74515Notes

Reaction equation

HRID 74515 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=O)[C:11]2([CH3:19])[CH3:18].O>C1COCC1>[F:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH2:12][C:11]2([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 451394095-Fluoro-3,3-dimethylindolin-2-one

Product 1

HCID 217125755-Fluoro-3,3-dimethylindoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
70 °C

Procedure

Under an argon atmosphere a solution of 9.30 mL (9.30 mmol) of a 1M solution lithium aluminium hydride in THF and 10 mL THF was slowly added dropwise to 1.40 g (7.81 mmol) 5-fluoro-3,3-dimethyl-1,3-dihydroindol-2-one in 50 mL THF. Then the reaction mixture was heated to 70° C. for 1 h. After cooling 2 mL water were added. The solution was dried on sodium sulphate and filtered off. The solvent was eliminated i. vac.

Workup

  1. additionwere added
  2. customThe solution was dried on sodium sulphate
  3. filtrationfiltered off

Sources & evidence

ORD record
ord-c075ca5d5e0c4fa8982e071636fca851
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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