Reaktion #339134

Reaktionsgleichung

ethyl 2-methoxyimino-5-methyl-4-oxohexanoate

3-chloro-2-hydrazinopyridine

tetrahydrofuran

→

ethyl 1-(3-chloro-2-pyridinyl)-3-isopropyl-1H-pyrazole-5-carboxylate

Ausbeute 26.1%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux for 4 hours
3. 3
   EinengenThe reaction mixture was concentrated under reduced pressure
4. 4
   workup.ADDITIONWater was poured into the residue
5. 5
   Extraktionthe mixture was extracted with methyl t-butyl ether two times
6. 6
   WaschenThe combined organic layer was washed successively with a 1N aqueous sodium hydroxide solution, water
7. 7
   Trocknenan aqueous saturated chloride solution, dried over anhydrous magnesium sulfate
8. 8
   Einengenconcentrated under reduced pressure

Vorschrift

A mixture of 3.0 g of ethyl 2-methoxyimino-5-methyl-4-oxohexanoate, 2.4 g of 3-chloro-2-hydrazinopyridine, 50 ml of tetrahydrofuran and 100 ml of acetic acid was stirred at room temperature for 20 hours, and then heated to reflux for 4 hours. The reaction mixture was concentrated under reduced pressure. Water was poured into the residue, and the mixture was extracted with methyl t-butyl ether two times. The combined organic layer was washed successively with a 1N aqueous sodium hydroxide solution, water and an aqueous saturated chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.07 g of ethyl 1-(3-chloro-2-pyridinyl)-3-isopropyl-1H-pyrazole-5-carboxylate of the formula:

Quelle