Oxindole → HCID 69659233, compound

HRID 1829050Notes

Reaction equation

HRID 1829050 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:21]1([C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]([CH2:31][C:32]([OH:34])=[O:33])[O:23]1)=O>COCCOC>[O:10]=[C:2]1[C:3](=[C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]([CH2:31][C:32]([OH:34])=[O:33])[O:23]2)[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1]1

Participants

5

Reactant 3

HCID 321710OxindoleHCID 5897301,3-Dihydro-3-oxo-1-isobenzofuranacetic acidHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 69659233HCID 69659233, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of oxindole (0.400 g, 3.0 mmol) in DME (8.0 mL) was added 9.0 mL LHMDS (1.0 M in THF). After stirring at room temperature for 10 min, phthalide-3-acetic acid (0.519 g, 2.7 mmol) was added as a solid in one portion. The mixture was rapidly stirred for 3.5 h and then quenched into 4% HCl aqueous solution (100 mL) to give a yellow solid. The solid was filtered, rinsed with H2O, MeOH and then 6:4/hexane:EtOAc to afford (0.105 g, 13%) of product as a yellow solid.

Workup

  1. stirringThe mixture was rapidly stirred for 3.5 h
  2. customquenched into 4% HCl aqueous solution (100 mL)
  3. customto give a yellow solid
  4. filtrationThe solid was filtered
  5. washrinsed with H2O, MeOH

Sources & evidence

ORD record
ord-a4ebdf4bb9fc482085ede03cdd6e35e5
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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