1-Pent-4-enyl-azocan-2-one → 4-(2-Oxo-azocan-1-yl)-butyraldehyde

HRID 10180

反应方程式

HRID 10180 反应方程式
[CH2:1]([N:6]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:14])[CH2:2][CH2:3][CH:4]=C.I([O-])(=O)(=O)=[O:16].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[O:14]=[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:6]1[CH2:1][CH2:2][CH2:3][CH:4]=[O:16]

参与物

6

反应物 2

HCID 219785471-Pent-4-enyl-azocan-2-oneHCID 23667635高碘酸钠

产物 1

HCID 219785824-(2-Oxo-azocan-1-yl)-butyraldehyde收率 0%

试剂、催化剂与溶剂 3

HCID 30318锇酸催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8028四氢呋喃溶剂

实验过程

Osmium tetroxide (17 mg, 0.07 mmole) was added to 1-pent-4-enyl-azocan-2-one (5.52 g, 28.3 mmole) in a mixture of tetrahydrofuran (100 mL) and water (50 mL) under ambient water bath cooling. The mixture was stirred for 5 minutes and solid sodium periodate (15.11 g, 70.65 mmole) was added in portions over 15 minutes. The reaction mixture was stirred for 3 hours and filtered. The filtrate was concentrated, saturated with solid sodium chloride, and extracted with methylene chloride. The organic phase was dried (magnesium sulfate) and concentrated. Purification by silica gel chromatography, eluting with chloroform, gave 4-(2-oxo-azocan-1-yl)-butyraldehyde (4.72 μg).

后处理

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred for 3 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated, saturated with solid sodium chloride
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic phase was dried (magnesium sulfate)
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography
  9. washeluting with chloroform

来源与证据

ORD记录
ord-42201cf9f09346ee95bb09f0fe591bf4
来源数据集
uspto-grants-2006_08
专利号
US07094778B2

关联笔记

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