Ammonium Chloride → HCID 117759923, compound

HRID 1049553Notes

Reaction equation

HRID 1049553 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[C:10]([O:12][Si](C(C)C)(C(C)C)C(C)C)[CH:9]=[CH:8][C:7]=1[C:23]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:24]=1[F:31])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>C1COCC1>[C:1]([O:5][C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:7]=1[C:23]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:24]=1[F:31])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 131736026HCID 131736026, compound

Product 1

HCID 117759923HCID 117759923, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, to a solution of ((2-(tert-butoxy)-2′-fluoro-5′-methoxy-[1,1′-biphenyl]-4-yl)oxy)triisopropylsilane (96.2 mg) in THF (1.44 mL) was added a 1 M solution (431 μL) of tetrabutylammonium fluoride in THF at room temperature, and the mixture was stirred for 1 hr. The reaction mixture was poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with 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 (56.1 mg) as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-f9df91f0fb404e34b2d8ab2e64870382
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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