反応 #566652

反応方程式

trifluoroacetaldehyde ethyl hemiacetal

p-toluamide

dioxane

→

desired product

収率 81.7%

4-methyl-N-(2,2,2-trifluoro-1-hydroxyethyl)benzamide

収率 81.7%

溶媒

ethyl acetate

反応条件

後処理

1. 1
   温度heated
2. 2
   温度at reflux for 44 hours
3. 3
   温度The homogeneous solution was cooled
4. 4
   濃縮concentrated in vacuo
5. 5
   その他to provide a white solid
6. 6
   洗浄eluted through a medium porosity fritted filter funnel (
7. 7
   洗浄elution with 25% ethyl acetate/hexanes

実験手順

A 500 mL round-bottom flask was charged with trifluoroacetaldehyde ethyl hemiacetal (12.3 g, 85.0 mmol), p-toluamide (10.0 g, 74.0 mmol), and dioxane (150 mL). The thick white slurry was stirred at ambient temperature for 3 hours, then heated at reflux for 44 hours. The homogeneous solution was cooled and concentrated in vacuo to provide a white solid. The crude material was dissolved in ethyl acetate (50 mL), adsorbed onto silica gel (50 g), and eluted through a medium porosity fritted filter funnel (elution with 25% ethyl acetate/hexanes, then ethyl acetate) to provide 14.1 g of the desired product as a white solid.

出典