Reaktion #710500

Reaktionsgleichung

2-chloro-6-(trifluoromethyl)nicotinaldehyde

sodium hydroxide

nitro methane

→

1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol

Ausbeute 72.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   SonstigeAfter completion of reaction
3. 3
   Einengenthe reaction mixture was concentrated under reduced pressure
4. 4
   Sonstigeto remove nitro methane
5. 5
   Sonstigequenched with ice water (500 mL)
6. 6
   Extraktionextracted with ethyl acetate (2×1.0 L)
7. 7
   WaschenThe combined organic layer was washed with water (500 mL), brine (500 mL)
8. 8
   Trocknendried over anhydrous sodium sulfate
9. 9
   Einengenconcentrated under reduced pressure

Vorschrift

To a stirred solution of 2-chloro-6-(trifluoromethyl)nicotinaldehyde (Int-17) (70 g, 1.0 eq.) in nitro methane (700 mL) was added sodium hydroxide (6.7 g, 0.5 eq.) at room temperature. The resulting reaction mixture was heated to 100° C. and stirred for 2 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was concentrated under reduced pressure to remove nitro methane quenched with ice water (500 mL) and extracted with ethyl acetate (2×1.0 L). The combined organic layer was washed with water (500 mL), brine (500 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to get pure 1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol (Int-18) (65.0 g, 72.0%).

Quelle