Triethylsilane → 5-Ethyl-1,3-dihydro-2H-indol-2-one

HRID 1840792Notes

Reaction equation

HRID 1840792 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)(=O)[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)[CH3:2]

Participants

4

Reactant 2

HCID 12052Triethylsilane2×HCID 102196435-acetyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 101541895-Ethyl-1,3-dihydro-2H-indol-2-oneYield 71%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To 5-Acetyl-2-oxindole (2 g) in 15 mL of trifluoroacetic acid in an ice bath was slowly added 1.8 g of triethylsilane; the reaction was then stirred at room temperature for 5 hours. One mL of triethylsilane was added and the stirring continued overnight. The reaction mixture was poured into ice water and the resulting precipitate collected by vacuum filtration, washed copiously with water and dried under vacuum to give 1.3 g (71% yield) of the title compound as a yellow solid.

Workup

  1. customthe stirring continued overnight
  2. filtrationthe resulting precipitate collected by vacuum filtration
  3. washwashed copiously with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-05c2ad0ad6fa471389aad6114bc0a554
Source dataset
uspto-grants-2004_01
Patent number
US06683082B2

Reaction notes

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