4'-Fluoroacetophenone → 1-(4-Fluorophenyl)ethanol

HRID 1855126Notes

Reaction equation

HRID 1855126 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.CC1C=CC(C(C)C)=CC=1.CC1C=CC(C(C)C)=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 98284'-FluoroacetophenoneHCID 10340Sodium Carbonate

Product 1

HCID 739461-(4-Fluorophenyl)ethanol

Reagents, catalysts & solvents 2

HCID 10908223Dichloro(p-cymene)ruthenium(II) dimerCatalystHCID 312751,4-DioxaneSolvent3×

Conditions

Temperature
105 °C

Procedure

Dichloro(p-cymene)ruthenium(II) dimer (1.2 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=i-Pr, Ar=C6H5—, 2.6 μmol, 0.65 mol %) were dissolved in 1,4-dioxane (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 105° C. After the mixture was cooled to room temperature, p-fluoroacetophenone (0.4 mmol), 1,4-dioxane (2 mL) and a solution of sodium carbonate in 1,4-dioxane (0.8 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 24 h under H2 (5 atm) at 10° C. The solvent was removed under reduced pressure, and the resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5). Accordingly, pure 1-(p-fluorophenyl)ethanol was obtained and the ee value (ee=98%) was measured by GC analysis.

Workup

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 24 h under H2 (5 atm) at 10° C
  4. customThe solvent was removed under reduced pressure
  5. customthe resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5)

Sources & evidence

ORD record
ord-2f0c03481d18406eb0e36b071c5dfe6c
Source dataset
uspto-grants-2015_02
Patent number
US08962852B2

Reaction notes

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