Water → HCID 15063386, compound

HRID 863694Notes

Reaction equation

HRID 863694 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][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].O>CN(C)C=O>[CH2:25]([O:24][C:22]([CH2:21][CH2:20][CH2:19][CH2:18][N: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])=[O:23])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 73125Ethyl indole-2-carboxylateHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 15063386HCID 15063386, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 18.9 g of ethyl indole-2-carboxylate in 100 ml of dimethylformamide was added to a suspension of 2.64 g of sodium hydride in 50 ml of dimethylformamide. After 1 hour, a solution of 20.9 g of ethyl 5-bromovalerate in 100 ml of dimethylformamide was added dropwise. After 48 hours, the mixture was poured into water, extracted with dichloromethane and the combined dichloromethane extracts were washed with water, dried and concentrated to give 26.2 g of ethyl 1-(4-ethoxycarbonylbutyl)indole-2-carboxylate.

Workup

  1. waitAfter 48 hours
  2. extractionextracted with dichloromethane
  3. washthe combined dichloromethane extracts were washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fe8c0d6ac6fd4942b48145b3bfa572c2
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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