6-Chloro-1,3-dihydroindol-2-one → Z-3-[4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butylidene]-6-chloro-1,3-dihydro-indol-2-one

HRID 2065409Notes

Reaction equation

HRID 2065409 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:12]([Si:16]([CH3:26])([CH3:25])[O:17][CH2:18][C:19]([CH3:24])([CH3:23])[CH2:20][CH:21]=O)([CH3:15])([CH3:14])[CH3:13].C[O-].[Na+]>CO>[C:12]([Si:16]([CH3:25])([CH3:26])[O:17][CH2:18][C:19]([CH3:24])([CH3:23])[CH2:20]/[CH:21]=[C:6]1\[C:7](=[O:11])[NH:8][C:9]2[C:5]\1=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 104896714-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyraldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 86656668Z-3-[4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butylidene]-6-chloro-1,3-dihydro-indol-2-oneYield 85.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the mixture of 6-chlorooxindole (2.1 g, 12.6 mmol) (Crescent) and 4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butyraldehyde (2.9 g, 12.6 mmol) in methanol (80 mL) was added a methanolic solution (25%, Aldrich) of sodium methoxide (4.08 g, 18.9 mmol) dropwise. The reaction mixture was stirred at room temperature for 10 min. The solvent was removed, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography (20% EtOAc in hexanes) to give E/Z-3-[4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butylidene]-6-chloro-1,3-dihydro-indol-2-one as a yellow oil (Yield 4.1 g, 84%).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9a1a800f81fe439da393717fe4096749
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

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