反应 #3098

反应方程式

diazomethane

Hydrogen chloride

dioxane

oxalyl chloride

2-propylpentanoic acid

→

1-Chloro-3-propyl-2-hexanone

溶剂

DMF

dichloromethane

反应条件

后处理

1. 1
   温度while warming to ambient temperature
2. 2
   温度The mixture was cooled to 0° C.
3. 3
   workup.STIRRINGThe reaction mixture was stirred 18 hours
4. 4
   温度while warming to ambient temperature
5. 5
   洗涤The reaction mixture was washed with 1M aqueous sodium carbonate solution (30 mL)
6. 6
   干燥dried over anhydrous sodium sulfate
7. 7
   过滤filtered
8. 8
   浓缩concentrated under reduced pressure
9. 9
   workup.DISSOLUTIONThe residue was dissolved in ether (2mL)
10. 10
    温度cooled to 0° C. under a nitrogen atmosphere
11. 11
    workup.STIRRINGThe reaction was stirred 18 hours
12. 12
    温度while warming to ambient temperature
13. 13
    浓缩The reaction mixture was concentrated under reduced pressure
14. 14
    其他the residual oil was used in the next step without further purification

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 (2mL) 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.

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