Reacción #1824336

Ecuación de reacción

Lawsone

3,3-dimethyl-butanal

pyrrolidine

→

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

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction for a further 20 minutes
2. 2
   OtroThe 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
   TemperaturaThe mixture was refluxed for 1 hour
5. 5
   Temperaturacooled
6. 6
   workup.ADDITIONthen diluted with ether before the organic phase
7. 7
   Lavadowas washed with sodium bicarbonate solution
8. 8
   Lavadowash with dilute HCl and one
9. 9
   Lavadowash with water
10. 10
    Otroby drying under vacuum
11. 11
    OtroThe product was purified by chromatograpy
12. 12
    Otrocrystallised from methanol
13. 13
    Otroto yield 260 mg

Procedimiento

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.

Fuente