Lithium Chloride → HCID 117760124, compound

HRID 1049605Notes

Reaction equation

HRID 1049605 reaction equation
[Cl-].[Li+].C[Si](C[Mg]Cl)(C)C.[CH:10]([Mg]Br)([CH3:12])[CH3:11].[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[C:24]1[C:25]([CH:40]=[O:41])=[CH:26][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[CH:28][CH:29]=1>C1COCC1.[Cl-].[Zn+2].[Cl-]>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[CH:26][C:25]=1[CH:40]([OH:41])[CH:10]([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 433294Lithium ChlorideHCID 1177599142'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-carbaldehydeHCID 178418365HCID 178418365, compoundHCID 178418680HCID 178418680, compound

Product 1

HCID 117760124HCID 117760124, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent4×

Procedure

Under a nitrogen atmosphere, to a solution of zinc chloride (35.9 mg) and lithium chloride (61.4 mg) in THF (976 μL) was added a 1 mol/L solution (527 μL) of trimethylsilylmethylmagnesium chloride in THF at room temperature, and the mixture was stirred for 15 min. To the reaction mixture was added a 1 mol/L solution (1449 μL) of isopropylmagnesium bromide in THF at room temperature, and the mixture was stirred for 45 min. Furthermore, to the reaction mixture was added dropwise a solution of 2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-carbaldehyde (160.9 mg) in THF (1952 μL) at 0° C., and the mixture was stirred for 1 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 (112 mg) as a colorless oil.

Workup

  1. stirringthe mixture was stirred for 45 min
  2. stirringthe mixture was stirred for 1 hr
  3. additionTo the reaction mixture was added, at 0° C.
  4. extractionsaturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-172dae75b2054120b80c2230471c15c4
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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