[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2I)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])(C)(C)C.CCCCC.CN(C)CCN(C)C.CN(C)[CH:40]=[O:41]>CCOCC.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[CH:40]=[O:41])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1To a solution of 7-benzyloxy-1-iodo-naphthalene (4.60 g, 12.77 mmol) in ether (120 mL) is added 1.7 M tert-butyl-lithium in pentane (8.26 mL, 14.0 mmol) at −78° C. under nitrogen atmosphere and the resulting mixture is stirred for one hour while being warmed up to 5° C. The mixture is cooled to −78° C. again before tetramethylethylene-diamine (1.93 mL, 1.49 g, 12.79 mmol) is added. The mixture is stirred for 10 minutes before N, N-dimethylformamide (0.99 mL, 0.93 g, 12.78 mmol) is added. The mixture is gradually warmed up to room temperature and stirred over night. Ethyl acetate is added to reaction mixture, washed with saturated ammonium chloride, dried over sodium sulfate, filtered and concentrated. The crude product is purified by silica gel chromatography (Hexanes/EtOAc=20/1) to give 7-benzyloxy-naphthalene-1-carbaldehyde (1.95 g, 58.3% yield); 1H NMR 400 Hz (CDCl3) δ 5.27 (s, 2H), 7.33 (m, 2H), 7.42 (m, 2H), 7.52 (m, 3H), 7.83 (d, J=8.98 Hz, 1H), 7.95 (d, J=7.11 Hz, 1H), 8.03 (d, J=8.10 Hz, 1H), 10.32 (s, 1H); MS m/z (M+H+) 263.05.
Wird geladen…
