反应 #1824336

反应方程式

Lawsone

3,3-dimethyl-butanal

pyrrolidine

→

2-(3.3-dimethyl-but-1-enyl)-3-hydroxy-naphthalene-1.4- dione

溶剂

THF

反应条件

后处理

1. 1
   其他the reaction for a further 20 minutes
2. 2
   其他The solvent was removed under vacuum
3. 3
   workup.DISSOLUTIONthe residue dissolved in benzene (40 ml) before addition of p-toluenesulphonic acid (2.3 g)
4. 4
   温度The mixture was refluxed for 1 hour
5. 5
   温度cooled
6. 6
   workup.ADDITIONthen diluted with ether before the organic phase
7. 7
   洗涤was washed with sodium bicarbonate solution
8. 8
   洗涤wash with dilute HCl and one
9. 9
   洗涤wash with water
10. 10
    其他by drying under vacuum
11. 11
    其他The product was purified by chromatograpy
12. 12
    其他crystallised from methanol
13. 13
    其他to yield 260 mg

实验过程

Lawsone (2-hydroxynaphthalene-1,4-dione) (1.4 g) and 3,3-dimethyl-butanal (1.0 g) were dissolved in 20 ml THF at room temperature and 795 μl pyrrolidine added before stirring the reaction for a further 20 minutes. The solvent was removed under vacuum and the residue dissolved in benzene (40 ml) before addition of p-toluenesulphonic acid (2.3 g). The mixture was refluxed for 1 hour, cooled then diluted with ether before the organic phase was washed with sodium bicarbonate solution, followed by one wash with dilute HCl and one wash with water followed by drying under vacuum. The product was purified by chromatograpy using 10% EtOAc/petroleum ether eluant and then crystallised from methanol to yield 260 mg; m.p. 126-128° C.

来源