反应 #41171

反应方程式

Cyclohexyl-hydrazine hydrochloride

2-dimethylaminomethylene-4,4,4-trifluoro-3-oxo-butyric acid ethyl ester

sodium acetate

→

1-cyclohexyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester

收率 58.5%

溶剂

ethanol

反应条件

后处理

1. 1
   温度After cooling to room temperature
2. 2
   其他the reaction mixture was partitioned between methylene chloride and water
3. 3
   洗涤The organic phase was washed with water and brine
4. 4
   萃取Each aqueous phase was back extracted with a second portion of methylene chloride
5. 5
   干燥dried over sodium sulfate
6. 6
   浓缩concentrated in vacuo
7. 7
   其他Purification by flash chromatography
8. 8
   洗涤eluting with a 5-40% ethyl acetate-hexanes

实验过程

Cyclohexyl-hydrazine hydrochloride (0.276 g, 1.59 mmol, CAS #24214-73-1, purchased from Aldrich), 2-dimethylaminomethylene-4,4,4-trifluoro-3-oxo-butyric acid ethyl ester (0.459 g, 1.67 mmol) and anhydrous sodium acetate (0.188 g, 2.29 mmol) were combined in ethanol (2.9 mL) and heated at 70° C. for 15 hours. After cooling to room temperature, the reaction mixture was partitioned between methylene chloride and water. The organic phase was washed with water and brine. Each aqueous phase was back extracted with a second portion of methylene chloride. The two organic phases were combined, dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography, eluting with a 5-40% ethyl acetate-hexanes gradient, yielded 1-cyclohexyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.270 g, 55%). Mass spectrum: m/z: 291.3 (M+H).

来源