反应详情

In a 25-mL, three-necked, round-bottomed flask equipped with nitrogen inlet, 3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazole (0.18 g, 1.0 eq.) was dissolved in DMF (5.0 mL, 27.0 V), and DABCO (0.143 g, 2.0 eq) and (Z)-1-(3,3-difluoroazetidin-1-yl)-3-iodoprop-2-en-1-one (0.192 g, 1.1 eq) were added. The reaction mixture was stirred at RT for 2-3 hr. The progress of the reaction was followed by TLC analysis on silica gel with 80% ethyl acetate-hexane as mobile phase, SM Rf==0.60 and Product Rf=0.4. Reaction mixture was poured in to ice water (50 mL) and extracted with EtOAc (3×25 mL). The combined organic layers were washed with brine solution (3×25 mL), dried over MgSO4, filtered, and concentrated by rotary evaporation (25° C., 20 mmHg) to afford 0.3 g of crude compound which was purified by column chromatography using silica 60/120 using ethyl acetate:hexane as mobile phase. The column (5×10 cm) was packed in hexane and started eluting in ethyl acetate in gradient manner starting with fraction collection (50-mL fractions) from 40% to 45% ethyl acetate in hexane. Compound started eluting with 40% ethyl acetate in hexane. Fractions containing such TLC profile were combined to obtain 70 mg of desired compound (yield 25.64%).

1. customIn a 25-mL, three-necked, round-bottomed flask equipped with nitrogen inlet
2. customReaction mixture
3. extractionextracted with EtOAc (3×25 mL)
4. washThe combined organic layers were washed with brine solution (3×25 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation (25° C., 20 mmHg)
8. customto afford 0.3 g of crude compound which
9. customwas purified by column chromatography
10. washstarted eluting in ethyl acetate in gradient manner
11. customstarting with fraction collection (50-mL fractions) from 40% to 45% ethyl acetate in hexane
12. washCompound started eluting with 40% ethyl acetate in hexane
13. additionFractions containing such TLC profile