Dichloromethane → 3-Benzylthiophene
Reaktionsgleichung
O[C:2]1([CH:13]=[CH:12][CH:11]=[CH:10][CH2:9]1)[CH2:3][C:4]1[CH:8]=[CH:7][S:6][CH:5]=1.ClCCl>[Na]>[CH2:3]([C:4]1[CH:8]=[CH:7][S:6][CH:5]=1)[C:2]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution containing P2I4 (3.42 g, 6 mmol) and 3-(1-hydroxybenzyl)thiophene (1.90 g, 10 mmol) in sodium-dried toluene (100 ml) was heated under nitrogen for one hour. The reaction mixture was cooled and then quenched with 10% aqueous sodium sulphite. The mixture was extracted with ether, and the combined organic phases were washed with water and brine then dried. Filtration and evaporation afforded a yellow oil, which on bulb-to-bulb distillation (110° C. at 0.05 mmHg) gave a pale-pink oil. Chromatography with dichloromethane gave 3-benzylthiophene as an oil (1.02 g, 53% yield); 1H nmr:delta 3.84 (2H,s), 7.0-7.2 (8H,m) ppm.