Reaktion #595860

Reaktionsgleichung

DABCO

3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazole

(Z)-isopropyl 3-iodoacrylate

→

(Z)-isopropyl 3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylate

Ausbeute 61.7%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 1 h
2. 2
   Extraktionextracted with EtOAc (3×1 L)
3. 3
   WaschenThe combined organic layers were washed with aqueous saturated sodium chloride solution (3×100 mL)
4. 4
   Trocknendried over anhydrous Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure (35° C., 20 mmHg)
7. 7
   Sonstigeto afford 250 g of the crude product that
8. 8
   Sonstigewas purified by column chromatography (60/120 silica gel)
9. 9
   Waschenthe desired compound started eluting from 2% EtOAC/n-hexane)
10. 10
    workup.ADDITIONFractions containing the desired compounds

Vorschrift

A 2 L 3-neck round-bottom flask was charged with a solution of 3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazole (160 g) in DMF (960 mL) The solution was treated with DABCO (127.74 g, 2 eq.) and stirred for 30 min before adding (Z)-isopropyl 3-iodoacrylate (150.32 g, 1.1 eq.) dropwise. After 1 h, the reaction mixture was poured into an ice-water slurry (5 L) and extracted with EtOAc (3×1 L). The combined organic layers were washed with aqueous saturated sodium chloride solution (3×100 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure (35° C., 20 mmHg) to afford 250 g of the crude product that was purified by column chromatography (60/120 silica gel) using ethyl acetate/n-hexane gradient (the column was packed in hexane and the desired compound started eluting from 2% EtOAC/n-hexane). Fractions containing the desired compounds were combined to afford (Z)-isopropyl 3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylate (138 g, yield: 61%).

Quelle