Ammonium Chloride → HCID 117760194, compound

HRID 1049603Notes

Reaction equation

HRID 1049603 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[F:23])=[C:11]([CH2:24][C:25]2([C:29]#[N:30])[CH2:28][CH2:27][CH2:26]2)[CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>C1COCC1>[F:23][C:16]1[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]=1[CH2:24][C:25]1([C:29]#[N:30])[CH2:26][CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 131736035HCID 131736035, compound

Product 1

HCID 117760194HCID 117760194, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-((4-((tert-butyl(dimethyl)silyl)oxy)-2′-fluoro-5′-methoxybiphenyl-2-yl)methyl)cyclobutanecarbonitrile (116 mg) in THF (5 mL) was added a solution (1 M, 0.54 mL) of tetrabutylammonium fluoride in THF, and the mixture was stirred at room temperature for 15 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract 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 (76 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and 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-0a46c566ffb342558b2bee50d477b72d
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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