3-Methoxyacetophenone → (+-)-1-(3-Methoxyphenyl)ethanol

HRID 1855122

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:11])[CH3:10])[CH:6]=[CH:7][CH:8]=1.C[O-].[Na+]>C(O)(C)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Cl-].[Ru+2]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([OH:11])[CH3:10])[CH:6]=[CH:7][CH:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

Tris(triphenylphosphine)ruthenium(II) chloride (3.8 mg, 4 μmol, 1 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 0.5 h at 85° C. After the mixture was cooled to room temperature, m-methoxyacetophenone (0.4 mmol), i-propanol (2 mL) and a solution of sodium methoxide in i-propanol (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 6 h under H2 (5 atm) at 40° 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 m-methoxyphenylethanol was obtained and the ee value (ee=99.2%) was measured by GC analysis.

Aufarbeitung

temperatureheated
temperatureAfter the mixture was cooled to room temperature
stirringstirred for 6 h under H2 (5 atm) at 40° 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)

Quellen und Nachweise

ORD-Eintrag: ord-bfe78a24955145f88ec3e6c5e4c5ac81
Quelldatensatz: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08962852B2

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