6-Chloro-1,3-dihydroindol-2-one → Z-3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentylidene]-6-chloro-1,3-dihydro-indol-2-one

HRID 2065415Notes

Reaction equation

HRID 2065415 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]([CH3:27])([CH3:26])[O:17][CH2:18][CH2:19][C:20]([CH3:25])([CH3:24])[CH2:21][CH:22]=O)([CH3:15])([CH3:14])[CH3:13].C[O-].[Na+]>CO>[C:12]([Si:16]([CH3:26])([CH3:27])[O:17][CH2:18][CH2:19][C:20]([CH3:25])([CH3:24])[CH2:21]/[CH:22]=[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 10942334Sodium MethoxideHCID 219327085-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentanal

Product 1

HCID 86656671Z-3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentylidene]-6-chloro-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the mixture of 6-chlorooxindole (3.3 g, 20 mmol) (Crescent) and 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentanal (6.5 g, 26.6 mmol) in methanol (150 mL) was added a methanolic solution (25%, Aldrich) of sodium methoxide (10 g, 46 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 (25-33% EtOAc in hexanes) to give E/Z-3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentylidene]-6-chloro-1,3-dihydro-indol-2-one as a off white solid (Yield 3.6 g, 46%).

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 (25-33% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2f5de777922e4ea7a85369aedbb6ecfd
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

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