Water → 4'-(Benzyloxy)-2-fluoro-5-methoxy-3'-(1-methoxy-3,3-dimethylbutyl)-1,1'-biphenyl

HRID 1049444Notes

Reaction equation

HRID 1049444 reaction equation
[CH2:1]([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])=[CH:11][C:10]=1[CH:24]([OH:30])[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:34].O>CN(C=O)C>[CH2:1]([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])=[CH:11][C:10]=1[CH:24]([O:30][CH3:34])[CH2:25][C:26]([CH3:27])([CH3:29])[CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1177597441-(4-(Benzyloxy)-2'-fluoro-5'-methoxy-[1,1'-biphenyl]-3-yl)-3,3-dimethylbutan-1-ol

Product 1

HCID 1177600444'-(Benzyloxy)-2-fluoro-5-methoxy-3'-(1-methoxy-3,3-dimethylbutyl)-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-(benzyloxy)-2′-fluoro-5′-methoxy-[1,1′-biphenyl]-3-yl)-3,3-dimethylbutan-1-ol (425 mg) prepared in Example 14, step C, in DMF (3.0 mL) was added 60% sodium hydride (100 mg), and the mixture was stirred at room temperature for 30 min. Iodomethane (443 mg) was added dropwise and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture, 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 to give the title compound as a crude product. This compound was used for the next step without further purification.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-63a71462cbce40a6b0c9c17bb00ec64e
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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