Sodium hydride → HCID 54297979, compound

HRID 365996Notes

Reaction equation

HRID 365996 reaction equation
[H-].[Na+].[CH2:3]([O:10][N:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][C:13]1=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:22]([O:24][CH:25]([O:28][CH2:29][CH3:30])[CH2:26]Br)[CH3:23]>CN(C)C=O>[CH2:3]([O:10][N:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:26][CH:25]([O:28][CH2:29][CH3:30])[O:24][CH2:22][CH3:23])[C:13]1=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 136088328HCID 136088328, compound

Product 1

HCID 54297979HCID 54297979, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.35 g of sodium hydride (60%) in 20 ml of N,N-dimethylformamide was added dropwise a solution of 2.00 g of 3-(benzyloxyimino)indolin-2-one in 20 ml of N,N-dimethylformamide at 0° C. in a nitrogen stream. After stirring the mixture at room temperature for 1 hour, 1.40 ml of bromoacetaldehyde diethyl acetal was added thereto, and the mixture was stirred for 12 hours at 70° C. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate and washed with an aqueous solution of sodium chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting crude product was purified by silica gel column chromatography (chloroform/methanol=100/1) to give 2.20 g (76%) of 3-(benzyloxyimino)-1-(2,2-diethoxyethyl)indolin-2-one.

Workup

  1. stirringthe mixture was stirred for 12 hours at 70° C
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with an aqueous solution of sodium chloride
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by silica gel column chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-b552c31d81744f6988fbc778e5aae34f
Source dataset
uspto-grants-2000_10
Patent number
US06127544

Reaction notes

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