반응 #1532724

반응 방정식

ethyl 1-(3-chloro-2-pyridinyl)-2,3-dihydro-3-oxo-1H-pyrazole-5-carboxyate

product

Ethyl 1-(3-chloro-2-pyridinyl)-2,3-dihydro-3-oxo-1H-pyrazole-5-carboxyate

potassium carbonate

propargyl bromide

water

→

title compound

수율 95.0%

Ethyl 1-(3-chloro-2-pyridinyl)-3-(2-propynyloxy)-1H-pyrazole-5-carboxylate

수율 95.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux for 15 minutes
3. 3
   온도The mixture was then cooled
4. 4
   추출extracted with a 1:1 mixture of diethyl ether and ethyl acetate
5. 5
   세척The organic extracts were then washed with a saturated solution of sodium chloride
6. 6
   건조dried over magnesium sulfate
7. 7
   농축The extract was concentrated to dryness on a rotary evaporator
8. 8
   기타chromatographed on silica gel

실험 절차

To a solution of ethyl 1-(3-chloro-2-pyridinyl)-2,3-dihydro-3-oxo-1H-pyrazole-5-carboxyate (i.e. the product of Example 1, Step B) (0.5 g, 1.9 mmol) in acetonitrile (20 mL) was added potassium carbonate (0.6 g, 3.8 mmol) and propargyl bromide (1.0 mL, 9.4 mmol). The reaction mixture was heated at reflux for 15 minutes. The mixture was then cooled and treated with water and extracted with a 1:1 mixture of diethyl ether and ethyl acetate. The organic extracts were then washed with a saturated solution of sodium chloride and dried over magnesium sulfate. The extract was concentrated to dryness on a rotary evaporator and chromatographed on silica gel using hexane/ethyl acetate (7:3) as eluent to isolate the title compound (0.45 g, 95% purity) as a red oil.

출처