반응 #88058

반응 방정식

3-fluoroisonicotinic acid

triethylamine

4-(2-phenyl-chroman-6-yloxy)-cyclohexanol

pivaloyl chloride

→

title compound

수율 68.4%

3-Fluoro-isonicotinic acid 4-(2-phenyl-chroman-6-yloxy)-cyclohexyl ester

수율 68.4%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타at 15° C
2. 2
   workup.STIRRINGStirring at room temperature
3. 3
   workup.WAITwas continued for 16 h
4. 4
   세척The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution
5. 5
   추출the aqueous layer extracted with dichloromethane
6. 6
   건조The combined organic layers were dried over sodium sulfate
7. 7
   여과filtered
8. 8
   기타the solvent removed by evaporation
9. 9
   기타The resulting oil was purified by reversed phase HPLC

실험 절차

To a solution of 158 mg of 3-fluoroisonicotinic acid (1.12 mmol) and 156 μl of triethylamine (1.12 mmol) in 16 ml of dichloromethane at 15° C. 138 μl of pivaloyl chloride (1.12 mmol) were added dropwise. The solution was stirred for 30 min. A solution of 110 mg of 4-(2-phenyl-chroman-6-yloxy)-cyclohexanol (0.34 mmol) in 4 ml of dichloromethane was added and 82 mg of 4-dimethylamino-pyridine (0.68 mmol) were added in one portion. Stirring at room temperature was continued for 16 h. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and filtered, and the solvent removed by evaporation. The resulting oil was purified by reversed phase HPLC. 104 mg of the title compound were isolated as solid (69%).

출처