Benzyl Bromide → HCID 11023142, Verbindung

Reaktionsgleichung

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:17]=[C:16]2[C:8]([C:9]3[C:10](=[O:18])[CH2:11][CH2:12][CH2:13][C:14]=3[NH:15]2)=[CH:7][CH:6]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([N:15]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10](=[O:18])[C:9]=2[C:8]2[C:16]1=[CH:17][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

Versuchsvorschrift

To a slurry of sodium hydride (0.26 g, 11 mmol) in dry DMF (50 mL) is added 7-methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one (2.2 g, 10.2 mmol). The mixture is stirred at room temperature for 30 min. To this is added benzyl bromide (1.3 mL, 11 mmol). The mixture is stirred at room temperature overnight. The mixture is partitioned between water and Et2O. The layers are separated and the organic layer washed twice with water (200 mL). The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography (200 mL) silica gel using CH3OH/CH2Cl2 (2/98) gave 1.7 g (55%) of the title compound; IR (drift) 1638, 1628, 1578, 1535, 1497, 1461, 1449, 1357, 1266, 1200, 1149, 1105, 834, 807, 700 cm−1. 1H NMR (CDCl3) δ2.2, 2.6, 2.8, 3.8, 6.7, 6.9, 7.0, 7.3, 8.1; Anal. Calcd for C20H19NO2: C, 78.66; H, 6.27; N, 4.59. Found: C, 78.29; H, 6.39; N, 4.53.