Trifluoroacetic acid → 5-Butyl-2-oxindole

HRID 457641Notes

Reaction equation

HRID 457641 reaction equation
C([SiH]([CH2:6][CH3:7])CC)C.[C:8]([C:13]1C=CC=[C:18]2[C:14]=1[CH2:15][C:16](=[O:22])[NH:17]2)(=O)[CH2:9][CH2:10][CH3:11].F[C:24](F)(F)C(O)=O>>[CH2:9]([C:8]1[CH:13]=[C:14]2[C:18](=[CH:6][CH:7]=1)[NH:17][C:16](=[O:22])[CH2:15]2)[CH2:10][CH2:11][CH3:24]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 545246444-Butanoyl-2-oxindole

Product 1

HCID 102197495-Butyl-2-oxindoleYield 91%

Procedure

Triethylsilane (2.3 g) was added to 2 g 4-butanoyl-2-oxindole in 20 mL of trifluoroacetic acid at room temperature and the solution stirred for 3 hours. The reaction was poured into ice water to give a red oil which solidified after standing. The solid was collected by vacuum filtration, washed with water and hexane and dried to give 1.7 g (91% yield) of the title compound as an off-white solid.

Workup

  1. customto give a red oil which
  2. filtrationThe solid was collected by vacuum filtration
  3. washwashed with water and hexane
  4. customdried

Sources & evidence

ORD record
ord-7d34e5d7fb6a42cf9b257d9d0bad3f2a
Source dataset
uspto-grants-2007_03
Patent number
US07189721B2

Reaction notes

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