Sodium Chloride → ethyl 1-[(2-ethoxycarbonylmethoxy)ethyl]-4-methyl-1H-indole-2-carboxylate

HRID 650078Notes

Reaction equation

HRID 650078 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=O)=O)=CC=1.[CH3:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[C:25]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[NH:26]2.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[CH3:19][CH2:18][O:17][C:15]([CH2:14][O:13][CH2:12][CH2:11][N:26]1[C:27]2[C:23](=[C:22]([CH3:21])[CH:30]=[CH:29][CH:28]=2)[CH:24]=[C:25]1[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:16]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 12529972Ethyl 4-methyl-1H-indole-2-carboxylateHCID 54462625Ethyl 2-(2-(tosyloxy)ethoxy)acetate

Product 1

HCID 54265658ethyl 1-[(2-ethoxycarbonylmethoxy)ethyl]-4-methyl-1H-indole-2-carboxylateYield 45.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of ethyl [2-(toluene-4-sulfonyloxy)ethoxy]acetate (3.90 g, 12.9 mmol) in N,N-dimethylformamide (10 ml) was added dropwise to a mixture of ethyl 4-methyl-1H-indole-2-carboxylate (2.50 g, 12.3 mmol), 60% sodium hydride (0.50 g, 12.5 mmol) and N,N-dimethylformamide (45 ml) at room temperature, and the resulting mixture was stirred at room temperature for 7 hours. The reaction mixture was poured into a 10% aqueous sodium chloride solution and extracted 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 1.86 g of ethyl 1-[(2-ethoxycarbonylmethoxy)ethyl]-4-methyl-1H-indole-2-carboxylate as a colorless oil.

Workup

  1. extractionextracted 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-12c5713c17454b35b92bb61488de417e
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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