Trimethylsilyl cyanide → 2-(2'-Fluoro-4-hydroxy-5'-methoxybiphenyl-2-yl)-4,4-dimethylpentanenitrile

HRID 1049588Notes

Reaction equation

HRID 1049588 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16]CC2C=CC(OC)=CC=2)=[CH:12][C:11]=1[CH:26](O)[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29].FC1C(B(C2C(F)=C(F)C(F)=C(F)C=2F)C2C(F)=C(F)C(F)=C(F)C=2F)=C(F)C(F)=C(F)C=1F.C[Si]([C:71]#[N:72])(C)C>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=1[CH:26]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:71]#[N:72]

Participants

6

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 582056Tris(pentafluorophenyl)boraneHCID 1177597911-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-yl)-3,3-dimethylbutan-1-ol

Product 1

HCID 1177598422-(2'-Fluoro-4-hydroxy-5'-methoxybiphenyl-2-yl)-4,4-dimethylpentanenitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-yl)-3,3-dimethylbutan-1-ol (160 mg) and tris(pentafluorophenyl)borane (20 mg) in acetonitrile (3 mL) was added trimethylsilyl cyanide (81 μL), and the mixture was stirred at room temperature for 1 hr. 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 (97 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-f33caba5c7ad49eab62ebe248a427f4b
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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