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Hydrochloric Acid → Ethyl 4-(3-heptanoyl-1-indolyl)butyrate

HRID 260835
Notes
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Reaction equation

HRID 260835 reaction equation
[C:1]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Br[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:10]=1)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 224004583-Heptanoylindole

Product 1

HCID 22400553Ethyl 4-(3-heptanoyl-1-indolyl)butyrate

Reagents, catalysts & solvents 2

HCID 6228Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-heptanoylindole (1.0 g) obtained in Pre. Ex. 1, ethyl 4-bromobutyrate (0.86 g) and potassium carbonate (1.0 g) in dimethyl formamide (DMF) (25 ml) was stirred at room temperature for 16 hours. The mixture was poured into a mixture of hydrochloric acid (100 ml) and ethyl acetate (AcOEt) (50 ml). The organic layer was washed with water, dried over MgSO 4 and evaporated. The residue was chromatographed on a silica gel column with a mixture of n-hexane and AcOEt (3:1) as eluent to give ethyl 4-(3-heptanoyl-1-indolyl)butyrate as a colorless oil. (1.53 g)

Workup

  1. customobtained in Pre
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO 4
  4. customevaporated
  5. customThe residue was chromatographed on a silica gel column with a mixture of n-hexane and AcOEt (3:1) as eluent

Sources & evidence

ORD record
ord-74c344ce48a447cb8bb88c5a8d3b223b
Source dataset
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05530019

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes