Triethylsilane → 5-Butyl-2-oxindole

HRID 1860838Notes

Reaction equation

HRID 1860838 reaction equation
C([SiH](CC)CC)C.[C:8]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[CH2:16]2)(=O)[CH2:9][CH2:10][CH3:11]>FC(F)(F)C(O)=O>[CH2:8]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])[CH2:16]2)[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 235593785-Butyryl-2-indolinone

Product 1

HCID 102197495-Butyl-2-oxindoleYield 91.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (2.3 g) was added to 2 g of 5-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 5-butyl-2-oxindole 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-e5bdc742b9ae45bfa82b5428e632d5f3
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

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