Sodium Hydroxide → 1-(2,4-Difluorophenyl)ethanol
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[F:11])=[O:3].[OH-].[Na+]>C(O)(C)C.CC1C=CC(C(C)C)=CC=1.CC1C=CC(C(C)C)=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[F:11][C:5]1[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:4]=1[CH:2]([OH:3])[CH3:1]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
Dichloro(p-cymene)ruthenium(II) dimer (1.2 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=t-Bu, Ar=C6H5—, 2.6 μmol, 0.65 mol %) were dissolved in i-propanol (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 85° C. After the mixture was cooled to room temperature, 2,4-difluoroacetophenone (0.4 mmol), i-propanol (2 mL) and an aqueous solution of sodium hydroxide (1.0 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 24 h under H2 (20 atm) at 0° 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-(2,4-difluorophenyl)ethanol was obtained and the ee value (ee=93%) was measured by GC analysis.
Workup
- temperatureheated
- temperatureAfter the mixture was cooled to room temperature
- stirringstirred for 24 h under H2 (20 atm) at 0° C
- customThe solvent was removed under reduced pressure
- customthe resultants were separated by column chromatography (silica gel column; eluent:ethyl acetate/petroleum ether=1/5)
Sources & evidence
- ORD record
- ord-9443cb19849a4bedacad7a0e35dacb0e
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962852B2
Reaction notes
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