N,N-Diethylaniline → Trimethylpsoralen
Reaktionsgleichung
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([CH3:17])[C:8]([O:12][CH2:13][C:14](Cl)=C)=[CH:9][CH:10]=2)[O:5][C:4](=[O:18])[CH:3]=1.[CH2:19](N(CC)C1C=CC=CC=1)C>CCOCC>[CH3:1][C:2]1[C:11]2[CH:10]=[C:9]3[C:8](=[C:7]([CH3:17])[C:6]=2[O:5][C:4](=[O:18])[CH:3]=1)[O:12][C:13]([CH3:14])=[CH:19]3Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 4,8-dimethyl-7-(2'-chloroallyloxy)coumarin (500 mg., 1.89 m mole) and N,N-diethylaniline (5.0 ml) was protected by an "Aquasorb" (TM), brand of phosphorous pentoxide drying tube, while being heated under reflux for twenty-four hours at an oil bath temperature of 220°-225° C. Treatment of the reaction mixture as described in part 1-B gave some black, ether-insoluble material which was discarded. The desired 4,5',8-trimethylpsoralene was obtained as a tan solid (154 mg., 41.6% yield), which was recrystallized from 95% ethanol to obtain light tan needles (53 mg., 14% yield) of m.p. 233° C. (rptd: m.p. 234° C.). Its infrared spectrum was identical to that of a commercial sample.