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

HRID 12609

反应方程式

HRID 12609 反应方程式
[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]

参与物

7

反应物 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798二甲基对苯二胺二盐酸HCID 58986251ethyl {3-[(2E)-but-2-en-1-yl]-2-oxocyclohexyl}acetate

产物 1

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

试剂、催化剂与溶剂 2

HCID 8028四氢呋喃溶剂2 次HCID 57417360Sodium chloride; water溶剂

反应条件

温度
0 °C

实验过程

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.

后处理

  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)

来源与证据

ORD记录
ord-edb649375269480abe9d8dfb97e80e8b
来源数据集
uspto-grants-2010_06
专利号
US07728022B2

关联笔记

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