p-Bromoacetophenone → 1-(4-Bromophenyl)ethanol

HRID 1855125

반응식

HRID 1855125 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C[O-].[Na+]>C(O)C.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]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 7466p-BromoacetophenoneHCID 10942334Sodium Methoxide

생성물 1

HCID 953521-(4-Bromophenyl)ethanol

시약·촉매·용매 2

HCID 84971Tris(triphenylphosphine)ruthenium(II) dichloride촉매HCID 702Ethanol용매3회

반응 조건

온도
80 °C

실험 절차

Tris(triphenylphosphine)ruthenium(II) chloride (3.8 mg, 4 μmol, 1 mol %) and a chiral ligand (M=Ru, R=n-Pr, Ar=C6H5—, 2.6 μmol, 0.65 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, p-bromoacetophenone (0.4 mmol), ethanol (2 mL) and a solution of sodium methoxide in ethanol (0.8 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 12 h under H2 (10 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=1/5). Accordingly, pure 1-(p-bromophenyl)ethanol was obtained and the ee value (ee=97%) was measured by GC analysis.

후처리

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 12 h under H2 (10 atm) at 25° 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-0ba645185a3c41928357a4933f988980
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962852B2

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