6-Nitro-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene → 7-Nitro-2-tetralone
Reaktionsgleichung
[N+:1]([C:4]1[CH:14]=[C:13]2[C:7]([CH2:8][CH2:9][CH:10]3[O:12][CH:11]32)=[CH:6][CH:5]=1)([O-:3])=[O:2]>C1C=CC=CC=1.[I-].[Zn+2].[I-]>[N+:1]([C:4]1[CH:14]=[C:13]2[C:7]([CH2:8][CH2:9][C:10](=[O:12])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
6-Nitro-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene (1.3 g, 6.8 mmol) was combined with anhydrous zinc iodide powder (1.0 g, 3.1 mmol) in benzene and stirred at rt under nitrogen in a dark vessel for 15 h. The reaction mixture was filtered and the filtrate concentrated under vacuum. The crude residue was purified by silica gel flash column chromatography (10-50% EtOAc/hexanes) to yield 750 mg (58%) of the desired ketone as a yellow powder. 1H NMR (400 MHz, DMSO-d6) δ 8.09 (d, J=2.1 Hz, 1H), 8.06 (dd, J=8.2, 2.4 Hz, 1H), 7.55 (d, J=8.3 Hz, 1H), 3.75 (s, 2H), 3.15 (t, J=6.7 Hz, 2H), 2.50-2.43 (m, 4H).