Ethyl Acetate → 2-Azido-1-(2-naphthyl)ethanone

Reaktionsgleichung

Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[N-:15]=[N+:16]=[N-:17].[Na+].CCOC(C)=O>CC(C)=O>[N:15]([CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4])=[N+:16]=[N-:17]

Komponenten

Versuchsvorschrift

To 2-bromo-1-(2-naphthyl)ethanone in acetone was added NaN3 (1 eq.) and the mixture was stirred at RT for 24 h. EtOAc was added (10 vol.) and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography on silica eluting with 10% EtOAc/Petroleum ether to obtain the product as a white solid. 1H NMR (300 MHz, CDCl3) δ: 8.39 (1H, s), 8.02-7.82 (4H, m), 7.69-7.50 (2H, m), 4.68 (2H, s). MS (ES) C12H9N3O requires: 211, found: 212 (M+H)+.