反応 #1966

反応方程式

3,4,5,6-tetrafluoro-2-picoline

LDA

LDA

hexane

ethyl iodide

→

title compound

2-Propyl-3,4,5,6-tetrafluoropyridine

溶媒

brine

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGAfter the reaction mixture is stirred at -60° C. for 0.5 hours
2. 2
   その他is allowed to slowly (1.5 hours)
3. 3
   温度warm to -30° C
4. 4
   抽出the aqueous mixture is extracted with methylene chloride
5. 5
   抽出The organic extract
6. 6
   乾燥is dried over anhydrous sodium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   workup.DISTILLATIONThe residue is distilled

実験手順

A 1.5M solution of LDA in hexane (100 mL, 150 mmol) is cooled to -60° C. in an isopropyl alcohol/dry ice bath. To the stirred LDA solution, under nitrogen, is added, dropwise over a 0.5 hours period, a solution of 22.617 g (137 mmol) of 3,4,5,6-tetrafluoro-2-picoline, the product of Step 1, in 80 mL of dry THF. The reaction mixture is stirred for 0.5 hours at -60° C. and then a solution of 10.95 mL (137 mmol) of ethyl iodide in 30 mL of dry THF is added, dropwise over a 20 minute period. After the reaction mixture is stirred at -60° C. for 0.5 hours, the cooling bath is allowed to slowly (1.5 hours) warm to -30° C. The reaction mixture is poured into cold brine and the aqueous mixture is extracted with methylene chloride. The organic extract is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue is distilled to afford the title compound.

出典