2-Acetylnaphthalene → alpha-Methylnaphthalene-2-methanol

HRID 1855133

Reaktionsgleichung

[CH3:1][C:2]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1)=[O:3].[OH-].[K+]>ClCCl.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]>[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH:2]([OH:3])[CH3:1]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

Tris(triphenylphosphine)ruthenium(II) chloride (3.8 mg, 4 μmol, 1 mol %) and a chiral ligand (M=Ru, R=t-Bu, Ar=3,5-t-Bu2C6H3—, 2.6 μmol, 0.65 mol %) were dissolved in dichloromethane (3 mL) under nitrogen atmosphere, and then heated and stirred for 0.5 h at 40° C. After the mixture was cooled to room temperature, 2-acetonaphthone (0.4 mmol), dichloromethane (2 mL) and an aqueous solution of potassium hydroxide (0.2 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 24 h under H2 (10 atm) at 50° 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-naphthyl)ethanol was obtained and the ee value (ee=98%) was measured by GC analysis.

Aufarbeitung

temperatureheated
temperatureAfter the mixture was cooled to room temperature
stirringstirred for 24 h under H2 (10 atm) at 50° 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-6014b161c2634b96a5b4faead481fbf1
Quelldatensatz: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08962852B2

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