1-Acetylnaphthalene → 1-(1-Naphthyl)ethanol

HRID 1855132

반응식

HRID 1855132 반응식
[CH3:1][C:2]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)=[O:3].CC(C)([O-])C.[K+]>O1CCOCC1.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].[Fe]>[C:4]1([CH:2]([OH:3])[CH3:1])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 2

HCID 136631-AcetylnaphthaleneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 980301-(1-Naphthyl)ethanol

시약·촉매·용매 3

HCID 23925Iron촉매HCID 84971Tris(triphenylphosphine)ruthenium(II) dichloride촉매HCID 312751,4-Dioxane용매3회

반응 조건

온도
105 °C

실험 절차

Tris(triphenylphosphine)ruthenium(II) chloride (3.8 mg, 4 μmol, 1 mol %) and a chiral ligand (M=Fe, R=Me, Ar=C6H5—, 2.6 μmol, 0.65 mol %) were dissolved in 1,4-dioxane (3 mL) under nitrogen atmosphere, and then heated and stirred for 2 h at 105° C. After the mixture was cooled to room temperature, 1-acetonaphthone (0.4 mmol), 1,4-dioxane (2 mL) and a solution of potassium t-butoxide in 1,4-dioxane (0.4 mL, 0.4 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 24 h under H2 (40 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-(1-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 (40 atm) at 0° 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-d8bd60830b21433195e3d279c575b9b1
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962852B2

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