Hydrogen Peroxide → 2-Ethyl (2-ethyl-7a-hydroxyoctahydro-1-benzofuran-7-yl)acetate

HRID 12609

반응식

HRID 12609 반응식
[CH2:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]1=[O:17])/[CH:2]=[CH:3]/[CH3:4].B.[OH-:19].[Na+].OO>O1CCCC1.[Cl-].[Na+].O>[CH2:3]([CH:2]1[CH2:1][CH:5]2[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]2([OH:19])[O:17]1)[CH3:4]

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 58986251ethyl {3-[(2E)-but-2-en-1-yl]-2-oxocyclohexyl}acetate

생성물 1

HCID 589862392-Ethyl (2-ethyl-7a-hydroxyoctahydro-1-benzofuran-7-yl)acetate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 57417360Sodium chloride; water용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of ethyl {3-[(2E)-but-2-en-1-yl]-2-oxocyclohexyl}acetate (565 mg, 2.37 mmol) in tetrahydrofuran (20 ml) at 0° C. was added borane.tetrahydrofuran complex (1 M in tetrahydrofuran, 3.56 ml, 3.56 mmol) and the reaction allowed to stir at 0° C. for 35 min. Sodium hydroxide (4N, 5.6 ml) and hydrogen peroxide (5.6 ml) were added and the reaction allowed to stir at room temperature for 1 h. Diluted with brine, then extracted three times with dichloromethane. The combined organics were washed twice with brine, dried over sodium sulfate, concentrated in vacuo and purified by column chromatography (50% EtOAc/hexanes). The desired title compound (345 mg) was obtained as a colourless oil as a complex mixture of diastereomers.

후처리

  1. stirringto stir at room temperature for 1 h
  2. extractionextracted three times with dichloromethane
  3. washThe combined organics were washed twice with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-edb649375269480abe9d8dfb97e80e8b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728022B2

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