Tetrabutylammonium Fluoride → HCID 131735828, compound

HRID 2206071Notes

Reaction equation

HRID 2206071 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:5](COCC[Si](C)(C)C)[CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>COCCOC.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH:5][CH:6]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131735829HCID 131735829, compound

Product 1

HCID 131735828HCID 131735828, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of ethyl (2E)-3-(4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrol-2-yl)acrylate (200 mg) obtained in Step C of Example 7 and tetra-n-butylammonium fluoride (698 mg) in DME (2 mL) was stirred at 85° C. for 2.5 hr. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (102 mg).

Workup

  1. washthe mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5414914db8d0405ba202c77b64084326
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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