[C:1]([Si:5]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH:16]=[CH:17][N+:18]([O-])=O)=[CH:11][C:10]=1[CH3:21])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[Si:5]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][CH2:17][NH2:18])=[CH:11][C:10]=1[CH3:21])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:6])[CH3:7]A solution of tert-butyl-[2,6-dimethyl-4-(2-nitrovinyl)phenoxy]dimethylsilane (0.20 g) in 15 mL diethyl ether was cooled to 0° C. Lithium aluminum hydride (0.20 g) was added in portions to the stirring nitroalkene solution. The resulting slurry was refluxed for 3 h and then cooled to 0° C. The mixture is carefully quenched by the sequential addition of 0.2 mL of water, followed by 0.2 mL of 3 N sodium hydroxide and 0.6 mL of water. The mixture was stirred for 15 min, then filtered to remove the aluminum salts. The filtrate was collected and the volatile material was removed by a rotary evaporator to give 100 mg of 2-[4-(tert-butyldimethylsilanyloxy)-3,5-dimethylphenyl]ethylamine.
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