(E)-1-(Benzyloxy)-4-(2-nitrovinyl)benzene → 2-(4-Benzyloxy-phenyl)-ethylamine

Participants

Reaction Steps

A solution of the product of Step B (1.06 g; 4.15 mmol) in anhydrous THF (20 ml) was added drop wise to a suspension of LiAlH4 (0.52 g; 13.7 mmol) in anhydrous THF (10 ml) over a period of 1 h at room temperature with vigorous stirring. After additional stirring for 2 h, the reaction mixture was quenched with H2O (1 ml), followed by 10% NaOH (2 ml) and H2O (1 ml). This was stirred for additional 30 min and precipitate formed was filtered off, washed with CH2Cl2 (3×20 ml) and combined filtrates were evaporated to dryness to give the crude title compound (0.71 g; 75%), as a creamy foam, which was used in the next step without further purification. 1H-NMR (CDCl3) 1.5 (broad s, 2H+H2O); 2.71 (tr, 2H, J=6.8 Hz); 2.94 (tr, 2H, J=6.8 Hz); 5.04 (s, 2H); 6.17-6.84 (m, 3H); 7.17-7.43 (m, 6H).

Provenance & Evidence