تفاعل #3098

معادلة التفاعل

diazomethane

Hydrogen chloride

dioxane

oxalyl chloride

2-propylpentanoic acid

→

1-Chloro-3-propyl-2-hexanone

المذيبات

DMF

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwhile warming to ambient temperature
2. 2
   درجة الحرارةThe mixture was cooled to 0° C.
3. 3
   workup.STIRRINGThe reaction mixture was stirred 18 hours
4. 4
   درجة الحرارةwhile warming to ambient temperature
5. 5
   غسيلThe reaction mixture was washed with 1M aqueous sodium carbonate solution (30 mL)
6. 6
   تجفيفdried over anhydrous sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   workup.DISSOLUTIONThe residue was dissolved in ether (2mL)
10. 10
    درجة الحرارةcooled to 0° C. under a nitrogen atmosphere
11. 11
    workup.STIRRINGThe reaction was stirred 18 hours
12. 12
    درجة الحرارةwhile warming to ambient temperature
13. 13
    تركيزThe reaction mixture was concentrated under reduced pressure
14. 14
    أخرىthe residual oil was used in the next step without further purification

الإجراء التجريبي

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.

المصدر