Hexane → 1-Benzyl-3-(ethoxycarbonylmethyl)-3-hydroxyindolin-2-one

HRID 1953307Notes

Reaction equation

HRID 1953307 reaction equation
C[Si](C)(C)N[Si](C)(C)C.CCCCCC.C([Li])CCC.[CH2:21]([N:28]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:31](=[O:32])[C:29]1=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:39]([O:42][CH2:43][CH3:44])(=[O:41])[CH3:40]>O1CCCC1.O>[CH2:21]([N:28]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:31]([CH2:40][C:39]([O:42][CH2:43][CH3:44])=[O:41])([OH:32])[C:29]1=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 5

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 13838HexamethyldisilazaneHCID 2647341-BenzylisatinHCID 178418339Butyllithium

Product 1

HCID 2645481-Benzyl-3-(ethoxycarbonylmethyl)-3-hydroxyindolin-2-oneYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.4 ml of 1,1,1,3,3,3-hexamethyldisilazane in 10 ml of dry tetrahydrofuran was added dropwise 6.4 ml of a 1.59M hexane solution of n-butyl lithium at -78° C. under a nitrogen atmosphere, followed by stirring at that temperature for 10 minutes. To the mixture was slowly added 0.976 ml of ethyl acetate, followed by stirring at -78° C. for 30 minutes. To the mixture was further added a solution of 2.00 g of 1-benzylisatin in 10 ml of dry tetrahydrofuran, followed by stirring at that temperature for 1 hour. Water was added to the reaction mixture, and the product was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate to give 2.23 g (81%) of the title compound.

Workup

  1. stirringby stirring at -78° C. for 30 minutes
  2. stirringby stirring at that temperature for 1 hour
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-ee4eb3c1dbf44d6da1bd5f0277ce81a7
Source dataset
uspto-grants-2000_09
Patent number
US06114536

Reaction notes

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