3-Acetylpyridine → alpha-Methyl-3-pyridinemethanol

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 tetrahydrofuran (3 mL) under nitrogen atmosphere, and then heated and stirred for 2 h at 65° C. After the mixture was cooled to room temperature, 3-acetylpyridine (0.4 mmol), tetrahydrofuran (2 mL) and a solution of potassium ethoxide in ethanol (0.1 mL, 0.2M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 6 h under H2 (50 atm) at 25° C. The solvent was removed under reduced pressure, and the resultants were separated by column chromatography (silica gel column; eluent:ethyl acetate/petroleum ether=1/1). Accordingly, pure 3-(1-hydroxyethyl)pyridine was obtained and the ee value (ee=93%) was measured by GC analysis.

Provenance & Evidence