Sodium hydride → HCID 54376915, compound

HRID 963102Notes

Reaction equation

HRID 963102 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[H-].[Na+].Br[CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>CN(C)C=O>[CH2:13]([O:12][C:10]([C:2]1[N:1]([CH2:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62576Benzyl bromoacetateHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 54376915HCID 54376915, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl indole-2-carboxylate (22 g) was dissolved in dimethylformamide (150 ml), and sodium hydride (including 60% oil, 5.12 g) was gradually added with stirring. Then, benzyl bromoacetate (19.2 ml) was added, and the mixture was stirred for 3 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was concentrated under reduced pressure. The residue thus obtained as a solid was subjected to silica gel column chromatography and eluted with a mixed solvent of ethyl acetate and hexane to give benzyl 2-ethoxycarbonyl-indole-1-acetate (28.9 g) as an oil. This compound (32.5 g) was dissolved in ethanol (350 ml), and hydrogenated in the presence of palladium/carbon (10%) catalyst at 1 atm. The catalyst was filtered off, and the solvent was concentrated under reduced pressure. The obtained residue was crystallized from isopropyl ether to give 10.22 g of 2-ethoxycarbonyl-indole-1-acetic acid.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customThe residue thus obtained as a solid
  7. washeluted with a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-d3b147ad810b4f0e89b85b2f8e841ee5
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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