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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence