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Ethanol → ethyl 4-{1-[2-(ethyloxy)-2-oxoethyl]-7-ethynyl-1H-indol-3-yl}butanoate

HRID 12626
Notes
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Reaction equation

HRID 12626 reaction equation
C(O)C.[CH2:4]([O:6][C:7](=[O:32])[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[C:18]#[C:19][Si](C)(C)C)[C:11]([CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:10]1)[CH3:5].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:4]([O:6][C:7](=[O:32])[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[C:18]#[CH:19])[C:11]([CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:10]1)[CH3:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 68692658ethyl 4-{1-[2-(ethyloxy)-2-oxoethyl]-7-[(trimethylsilyl)ethynyl]-1H-indol-3-yl}butanoate

Product 1

HCID 86622003ethyl 4-{1-[2-(ethyloxy)-2-oxoethyl]-7-ethynyl-1H-indol-3-yl}butanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ethanol (2 mL) solution of ethyl 4-{1-[2-(ethyloxy)-2-oxoethyl]-7-[(trimethylsilyl)ethynyl]-1H-indol-3-yl}butanoate (98 mg), potassium carbonate (50 mg) was added and the mixture was stirred at room temperature for 3 hours. To the reaction mixture, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and then concentrated to obtain the titled compound having the following physical properties (74 mg). Herein, ethyl 4-{1-[2-(ethyloxy)-2-oxoethyl]-7-[(trimethylsilyl)ethynyl]-1H-indol-3-yl}butanoate was prepared by the same operation as in Example 3, except for using ethyl 4-{7-bromo-1-[2-(ethyloxy)-2-oxoethyl]-1H-indol-3-yl}butanoate and ethynyl(trimethyl)silane.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-84f48ebed0bb446fb2cd7436530f7815
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728023B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes