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

HRID 1952919Notes

Reaction equation

HRID 1952919 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-b0c011b3e0bb4d9295614151459460e5
Source dataset
uspto-grants-2000_09
Patent number
US06114371

Reaction notes

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