Cyclohexanone, 3,3-dimethyl- → HCID 68523959, 화합물

HRID 237758

반응식

HRID 237758 반응식
[Mg].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:17][C:18]1([CH3:25])[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH2:19]1>BrC(Br)C.C1COCC1>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:20]2([OH:24])[CH2:21][CH2:22][CH2:23][C:18]([CH3:25])([CH3:17])[CH2:19]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 76322Cyclohexanone, 3,3-dimethyl-HCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 5462224Magnesium2회

생성물 1

HCID 68523959HCID 68523959, 화합물수율 53.4%

시약·촉매·용매 2

HCID 112011,1-Dibromoethane촉매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
60 °C

실험 절차

In a RB flask (250 mL) was placed magnesium turnings (2.08 g, 85.9 mmol), which were stirred under vacuum without solvent overnight. To the stirred magnesium turnings was added anhydrous THF (10 mL). To the resulting mixture at 50° C. was added several drops of dibromoethane, followed by 4-benzyloxybromobenzene (11.8 g, 42.9 mmol) in 40 ml of THF. After addition was complete, the reaction mixture was heated at 60° C. for 3 hours until a brownish-grey slurry was formed. The reaction mixture was cooled in an ice-bath and 3,3-dimethyl-cyclohexanone (3.87 g, 30.67 mmol) in THF (15 mL) was added dropwise. The reaction mixture was stirred at room temperature for one hour. The solvent was removed under reduced pressure. The residue was partitioned between EtOAc/aqueous NH4Cl. The aqueous phase was extracted three times with EtOAc. The organic phase was combined and dried (Na2SO4). Silica gel chromatography (EtOAc/heptane) provided 5.08 g of 1-(4-benzyloxy-phenyl)-3,3-dimethyl-cyclohexanol as a white solid.

후처리

  1. customIn a RB flask (250 mL) was placed
  2. additionAfter addition
  3. customwas formed
  4. temperatureThe reaction mixture was cooled in an ice-bath
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was partitioned between EtOAc/aqueous NH4Cl
  7. extractionThe aqueous phase was extracted three times with EtOAc
  8. dry with materialdried (Na2SO4)

출처 및 근거

ORD 기록
ord-59ab291a648c42589a51c0ae76ef90c9
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642603B2

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