Cyclohexanone → 1-(3-Tert-butyl-phenyl)-4-methylene-cyclohexanol

HRID 132104

반응식

HRID 132104 반응식
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].CCCCC.Br[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=1.[C:22]1(=[O:28])[CH2:27]CCC[CH2:23]1>O1CCCC1.[Cl-].[NH4+].C(OCC)(=O)C>[C:18]([C:14]1[CH:13]=[C:12]([C:22]2([OH:28])[CH2:27][CH2:3][C:1](=[CH2:4])[CH2:2][CH2:23]2)[CH:17]=[CH:16][CH:15]=1)([CH3:21])([CH3:20])[CH3:19]

참가 물질

8

반응물 4

HCID 7967CyclohexanoneHCID 8003PentaneHCID 3437981-Bromo-3-tert-butylbenzeneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 597337431-(3-Tert-butyl-phenyl)-4-methylene-cyclohexanol수율 81%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

실험 절차

A solution of 1.7 M tert-butyllithium in pentane (32.0 mL, 54.4 mmol) was added to a solution of 1-bromo-3-tert-butyl-benzene (5.54 g, 26.0 mmol) in tetrahydrofuran (60 mL) at −78° C. After stirring for 1 h, cyclohexanone (2.00 g, 18.2 mmol) in tetrahydrofuran (15 mL) was added. After stirring for 18 h, during which time the solution warmed to ambient temperature, the solution was diluted with saturated aqueous ammonium chloride and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 49:1, 24:1, 23:2 hexanes:ethyl acetate as the eluant to yield 3.61 g (81% yield) of 1-(3-tert-butyl-phenyl)-4-methylene-cyclohexanol as a yellow oil.

후처리

  1. stirringAfter stirring for 18 h, during which time the solution
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed with 49:1, 24:1, 23:2 hexanes

출처 및 근거

ORD 기록
ord-f0668dfcdcd04782a255a587cf61429e
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07385085B2

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