Water → 5-Fluoro-3,3-dimethylindoline

HRID 2059977Notes

Reaction equation

HRID 2059977 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 of 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-3635892b9abc4e23b95a316589fa94dd
Source dataset
uspto-grants-2012_10
Patent number
US08278336B2

Reaction notes

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