Tetrabutylammonium Fluoride → HCID 117759720, compound

HRID 1049579Notes

Reaction equation

HRID 1049579 reaction equation
[C:1](=[O:33])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([C:23]#[C:24][C:25]([CH3:32])([O:27][Si](C)(C)C)[CH3:26])[CH:9]=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[C:1](=[O:33])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([C:23]#[C:24][C:25]([OH:27])([CH3:32])[CH3:26])[CH:9]=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131736032HCID 131736032, compound

Product 1

HCID 117759720HCID 117759720, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2′-fluoro-5′-methoxy-2-(3-methyl-3-((trimethylsilyl)oxy)but-1-yn-1-yl)biphenyl-4-yl carbonate (480 mg) in THF (3 mL) was added a solution (1 M, 2.0 mL) of tetrabutylammonium fluoride in THF, and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (343 mg) as a colorless oil.

Workup

  1. washThe diluted solution was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a7bab61a1bb24dd5ae958e94e00de560
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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