Water → HCID 89404248, compound

Temperature

0 °C

In a 100 mL, 3N round-bottomed flask equipped with nitrogen inlet, thermometer pocket and stopper, 4-(3,5-bis(trifluoromethyl)phenyl)-1H-imidazole (1) (1.1 g, 1.0 eq.) was dissolved in dichloromethane (20 mL, 19V) the reaction mixture was cooled to 0° C. To this reaction mixture TEA (0.709 mL, 1.3 eq.) followed by Isopropyl acrylate (0.571 g, 1.3 eq.) was added at 0° C. and reaction mixture was stirred for 30 min. The progress of the reaction was followed by TLC analysis on silica gel with 20% Ethyl acetate-n-Hexane as mobile phase. Reaction mixture was poured into water (50 mL). The filtrate was extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine solution (3×50 mL), dried over MgSO4, filtered, and concentrated by rotary evaporation to afford 1.2 g of Crude compound which was purified by column chromatography. Product elute at 4% ethyl acetate in hexane to give 1.0 g of crude product (Cis 39%+Trans 56%) (Yield 65.35%).

1. customIn a 100 mL, 3N round-bottomed flask equipped with nitrogen inlet
2. additionwas added at 0° C.
3. customreaction mixture
4. customReaction mixture
5. extractionThe filtrate was extracted with EtOAc (3×20 mL)
6. washThe combined organic layers were washed with brine solution (3×50 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated by rotary evaporation
10. customto afford 1.2 g of Crude compound which
11. customwas purified by column chromatography
12. washProduct elute at 4% ethyl acetate in hexane

ORD record

ord-eadd282bfc954e7da671cebc9e9e94a1

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428490B2