تفاعل #41171

معادلة التفاعل

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

المردود 58.5%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling to room temperature
2. 2
   أخرىthe reaction mixture was partitioned between methylene chloride and water
3. 3
   غسيلThe organic phase was washed with water and brine
4. 4
   استخلاصEach aqueous phase was back extracted with a second portion of methylene chloride
5. 5
   تجفيفdried over sodium sulfate
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىPurification by flash chromatography
8. 8
   غسيلeluting with a 5-40% ethyl acetate-hexanes

الإجراء التجريبي

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).

المصدر