2-Acetylnaphthalene → alpha-Methylnaphthalene-2-methanol

HRID 1855133

반응식

HRID 1855133 반응식
[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]

참가 물질

5

반응물 2

HCID 71222-AcetylnaphthaleneHCID 14797Potassium Hydroxide

생성물 1

HCID 98243alpha-Methylnaphthalene-2-methanol

시약·촉매·용매 2

HCID 84971Tris(triphenylphosphine)ruthenium(II) dichloride촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
40 °C

실험 절차

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.

후처리

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 24 h under H2 (10 atm) at 50° C
  4. customThe solvent was removed under reduced pressure
  5. customthe resultants were separated by column chromatography (silica gel column; eluent: ethyl acetate/petroleum ether=1/5)

출처 및 근거

ORD 기록
ord-6014b161c2634b96a5b4faead481fbf1
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962852B2

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