反应 #341168

反应方程式

ethyl 2-(furan-2-yl)-2-hydroxyacetate

trimethylorthoacetate

hexanoic acid

NaOH

→

2,3-di(carboxymethyl)furan

溶剂

decalin

methanol

decalin

反应条件

后处理

1. 1
   温度The reaction is cooled
2. 2
   萃取extracted with methanol
3. 3
   其他to provide
4. 4
   其他The methanol is removed
5. 5
   其他the crude reaction
6. 6
   萃取is extracted with ether
7. 7
   萃取extracted with ethyl acetate
8. 8
   洗涤The organic layer is washed with brine
9. 9
   其他dried
10. 10
    浓缩concentrated

实验过程

A solution of ethyl 2-(furan-2-yl)-2-hydroxyacetate (11.05 g, 64.5 mmol), trimethylorthoacetate (29.8 mL, 387 mmol) and hexanoic acid (2 mL) in decalin (195 mL) is heated at 180° C. for 12 hours. The reaction is cooled and extracted with methanol to provide a mixture of diester and decalin. This mixture is dissolved in methanol (250 mL), cooled to 0° C., treated with 2 M NaOH (150 mL) and stirred for 12 hours. The methanol is removed and the crude reaction is extracted with ether, and the basic layer is acidified with 6 N HCl and extracted with ethyl acetate. The organic layer is washed with brine, dried and concentrated to give 2,3-di(carboxymethyl)furan.

来源