Sodium hydride → HCID 21714319, compound

HRID 650057Notes

Reaction equation

HRID 650057 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:23])=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14]2)(=O)=O.[H-].[Na+]>CN(C)C=O>[CH3:23][C:12]1[C:13]2[CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:16]3[CH2:6][CH2:7][O:8][C:9]([C:17]=23)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 21714287HCID 21714287, compound

Product 1

HCID 21714319HCID 21714319, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 7-(2-methanesulfonyloxy-ethoxy)-4-methyl-1H-indole-2-carboxylate (1.30 g, 3.81 mmol), 60% sodium hydride (0.15 g, 3.81 mmol) and N,N-dimethylformamide (65 ml) was stirred at room temperature for 8 hours. The reaction mixture was poured into ice water and extracted three times with ethyl acetate, and the extract solution was washed with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98) to obtain ethyl 2,3-dihydro-7-methyl-pyrrolo[1,2,3-de]-1,4-benzoxazine-5-carboxylate (0.87 g).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washthe extract solution was washed with a 5% aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98)

Sources & evidence

ORD record
ord-f8b86904411c41a4a754902b583de525
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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