Methyl iodide → Methyl 2-(2,2-dimethyl-1-(methyloxy)butyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662460Notes

Reaction equation

HRID 1662460 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]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]([OH:26])[C:21]([CH3:25])([CH3:24])[CH2:22][CH3:23].[H-].[Na+].I[CH3:30]>CN(C=O)C.CCOC(C)=O>[CH3:24][C:21]([CH3:25])([CH2:22][CH3:23])[CH:20]([C:11]1[CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[CH:15][C:10]=1[C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[F:1])[O:26][CH3:30]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57706901Methyl 2'-fluoro-2-(1-hydroxy-2,2-dimethylbutyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57706189Methyl 2-(2,2-dimethyl-1-(methyloxy)butyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylateYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 66.62A (0.39 g, 1.1 mmol) in DMF (5 mL), was added NaH (0.034 g, 1.4 mmol). The mixture was stirred at room temperature for 10 minutes and then iodomethane (0.20 mL, 3.2 mmol) was added. The mixture was stirred at room temperature for 60 minutes and then it was diluted with EtOAc, washed with water and brine, and dried over anhydrous Na2SO4. After removing solvent, the residue was purified by flash chromatography (silica gel, 1:9 EtOAc/hexane) and gave 66.62B, colorless oil, in 64% yield (260 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 60 minutes
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customAfter removing solvent
  5. customthe residue was purified by flash chromatography (silica gel, 1:9 EtOAc/hexane)

Sources & evidence

ORD record
ord-3cdb046a326d4194965b5649aff67847
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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