1-Iodopropane → 1-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)-[1,1'-biphenyl]-2-yl)-2,2-dimethylpentan-1-one

HRID 1049607Notes

Reaction equation

HRID 1049607 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][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:12][C:11]=1[C:26](=[O:30])[CH:27]([CH3:29])[CH3:28].[CH3:31][Si]([N-][Si](C)(C)C)(C)C.[Li+].I[CH2:42][CH2:43]C>C1COCC1>[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][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:12][C:11]=1[C:26](=[O:30])[C:27]([CH3:31])([CH3:28])[CH2:29][CH2:42][CH3:43]

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 1177599061-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)-[1,1'-biphenyl]-2-yl)-2-methylpropan-1-one

Product 1

HCID 1177599071-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)-[1,1'-biphenyl]-2-yl)-2,2-dimethylpentan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, to a solution of 1-(2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-yl)-2-methylpropan-1-one (128.6 mg) in THF (1574 μL) was added a solution (409 μL) of lithium bis(trimethylsilyl)amide in THF at 0° C., and the mixture was stirred for 10 min. To the reaction mixture was added 1-iodopropane (61.4 μL), and the mixture was stirred at room temperature for 2.5 hr. To the reaction mixture was added, at 0° C., 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 (65.9 mg) as a pale-yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 2.5 hr
  2. additionTo the reaction mixture was added, at 0° C.
  3. extractionsaturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-30d752d1691447969f426ee2e0db8a07
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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