Water → Benzyl 4-(3-nonyloxycarbonyl-1-indolyl)butyrate

HRID 260865Notes

Reaction equation

HRID 260865 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:11])=[CH:2]1.Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:13]([O:12][C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[CH:2]=1)=[O:11])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 3832489Benzyl 4-bromobutanoateHCID 22400454Nonyl indole-3-carboxylate

Product 1

HCID 22400555Benzyl 4-(3-nonyloxycarbonyl-1-indolyl)butyrateYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of nonyl indole-3-carboxylate (251 mg) obtained in Pre. Ex. 30, benzyl 4-bromobutyrate (449 mg) and potassium carbonate (362 mg) in N,N-dimethylformamide was stirred at 50° C. for 6 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and concentrated. Silica gel column chromatography of the concentrate afforded benzyl 4-(3-nonyloxycarbonyl-1-indolyl)butyrate (374 mg) as an oil.

Workup

  1. customobtained in Pre
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2b6370f1376b4f73a18d729362791ac3
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

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