Sodium Hydroxide → 1-(2,4-Difluorophenyl)ethanol

HRID 1855128노트

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HRID 1855128 반응식
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[F:11])=[O:3].[OH-].[Na+]>C(O)(C)C.CC1C=CC(C(C)C)=CC=1.CC1C=CC(C(C)C)=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[F:11][C:5]1[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:4]=1[CH:2]([OH:3])[CH3:1]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 677702,4-Difluoroacetophenone

생성물 1

HCID 146531531-(2,4-Difluorophenyl)ethanol

시약·촉매·용매 2

HCID 10908223Dichloro(p-cymene)ruthenium(II) dimer촉매HCID 3776Isopropanol용매2회

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온도
85 °C

실험 절차

Dichloro(p-cymene)ruthenium(II) dimer (1.2 mg, 2 μmol, 0.5 mol %) and a chiral ligand (M=Ru, R=t-Bu, Ar=C6H5—, 2.6 μmol, 0.65 mol %) were dissolved in i-propanol (3 mL) under nitrogen atmosphere, and then heated and stirred for 1 h at 85° C. After the mixture was cooled to room temperature, 2,4-difluoroacetophenone (0.4 mmol), i-propanol (2 mL) and an aqueous solution of sodium hydroxide (1.0 mL, 0.2 M) were added thereto. Thereafter, the reaction system was placed in an autoclave, and stirred for 24 h under H2 (20 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-(2,4-difluorophenyl)ethanol was obtained and the ee value (ee=93%) was measured by GC analysis.

후처리

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. stirringstirred for 24 h under H2 (20 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-9443cb19849a4bedacad7a0e35dacb0e
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962852B2

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