海萝胶 → 1-Chloro-3-propyl-2-hexanone

HRID 54573

反应方程式

HRID 54573 反应方程式
[CH2:1]([CH:4]([CH2:8][CH2:9][CH3:10])[C:5]([OH:7])=O)[CH2:2][CH3:3].C(Cl)(=O)[C:12]([Cl:14])=O.[N+](=C)=[N-].Cl.O1CCOCC1>ClCCl.CN(C=O)C>[Cl:14][CH2:12][C:5](=[O:7])[CH:4]([CH2:1][CH2:2][CH3:3])[CH2:8][CH2:9][CH3:10]

参与物

8

反应物 5

HCID 313海萝胶HCID 3121丙戊酸HCID 9550重氮甲烷HCID 312751,4-二氧六环HCID 65578草酰氯

产物 1

HCID 107973771-Chloro-3-propyl-2-hexanone

试剂、催化剂与溶剂 2

HCID 6228N,N-二甲基甲酰胺溶剂HCID 6344二氯甲烷溶剂

反应条件

温度
0 °C

实验过程

To 2-propylpentanoic acid (156.6 μl, 1.00 mmol) dissolved in anhydrous dichloromethane (2 mL) was added DMF (3 μL, 4 mole %), and the solution was cooled to 0° C. under a nitrogen atmosphere. To the solution was added oxalyl chloride (94.3 μL, 1.08 mmol) dropwise over a few minutes. The reaction was stirred 18 hours while warming to ambient temperature. The mixture was cooled to 0° C. and excess ~0.3M ethereal diazomethane solution was added. The reaction mixture was stirred 18 hours while warming to ambient temperature. The reaction mixture was washed with 1M aqueous sodium carbonate solution (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in ether (2 mL) and cooled to 0° C. under a nitrogen atmosphere. Hydrogen chloride as a 4N solution in dioxane (275 μL, 1.10 mmol) was added dropwise over a few minutes. The reaction was stirred 18 hours while warming to ambient temperature. The reaction mixture was concentrated under reduced pressure and the residual oil was used in the next step without further purification.

后处理

  1. temperaturewhile warming to ambient temperature
  2. temperatureThe mixture was cooled to 0° C.
  3. stirringThe reaction mixture was stirred 18 hours
  4. temperaturewhile warming to ambient temperature
  5. washThe reaction mixture was washed with 1M aqueous sodium carbonate solution (30 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe residue was dissolved in ether (2 mL)
  10. temperaturecooled to 0° C. under a nitrogen atmosphere
  11. stirringThe reaction was stirred 18 hours
  12. temperaturewhile warming to ambient temperature
  13. concentrationThe reaction mixture was concentrated under reduced pressure
  14. customthe residual oil was used in the next step without further purification

来源与证据

ORD记录
ord-6d229434942a420891095a2ee18e1ccd
来源数据集
uspto-grants-1997_04
专利号
US05622971

关联笔记

加载中…