反应 #41161

反应方程式

(Tetrahydro-pyran-4-yl)-hydrazine hydrochloride

ethyl (ethoxymethylene)-cyanoacetate

sodium acetate

→

5-amino-1-(tetrahydro-pyran-4-yl)-1H-pyrazole-4-carboxylic acid ethyl ester

收率 92.3%

溶剂

ethanol

反应条件

后处理

1. 1
   温度After cooling to room temperature
2. 2
   浓缩the reaction was concentrated
3. 3
   其他the residue was partitioned between methylene chloride and water
4. 4
   其他The organic phase was separated
5. 5
   洗涤washed with water
6. 6
   萃取Each aqueous phase was back extracted with methylene chloride
7. 7
   干燥dried over sodium sulfate
8. 8
   浓缩concentrated in vacuo
9. 9
   其他The crude material was purified by flash chromatography
10. 10
    洗涤eluting with 60-100% ethyl acetate/hexanes

实验过程

(Tetrahydro-pyran-4-yl)-hydrazine hydrochloride (1.975 g, 12.94 mmol), ethyl (ethoxymethylene)-cyanoacetate (1.958 g, 11.57 mmol) and sodium acetate (1.370 g; 16.70 mmol) were combined in ethanol (16 mL). The mixture was heated at 80-85° C. for 17 hours. After cooling to room temperature, the reaction was concentrated and the residue was partitioned between methylene chloride and water. The organic phase was separated and washed with water and then brine. Each aqueous phase was back extracted with methylene chloride. The two organic phases were combined, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography eluting with 60-100% ethyl acetate/hexanes to give 5-amino-1-(tetrahydro-pyran-4-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (2.554 g, 92%).

来源