1-Tetralone → 1,2,3,4-Tetrahydro-1-naphthalenol

Participants

Reaction Conditions

Reaction Steps

Tris(triphenylphosphine)ruthenium (II) chloride (1.9 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=i-Pr, Ar=C6H5—, 1.3 μmol, 0.33 mol %) were dissolved in ethanol (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 80° C. After the mixture was cooled to room temperature, 1-tetralone (0.4 mmol), ethanol (2 mL) and a solution of potassium hydroxide in ethanol (0.4 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 48 h under H2 (10 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 1,2,3,4-tetrahydro-1-naphthol was obtained and the ee value (ee=99.7%) was measured by GC analysis.

Provenance & Evidence