tert-Butyldimethyl(4-nitrophenoxy)silane → 4-((Tert-butyldimethylsilyl)oxy)aniline

Participants

Reaction Steps

A solution of 1-nitro4-(1,1,2,2-tetramethyl-1-silapropoxy)benzene (7.8 g, 30.8 mmol) (from Example 19a supra) and 10% Pd/C (0.70 g) (Aldrich) in ethyl acetate (100 mL) was hydrogenated for 1 day. The reaction mixture was filtered though Celite® and concentrated. The residue was purified by flash chromatography eluting with ethyl acetate/hexanes (1:9 V/N)) to afford 4-(1,1,2,2-tetramethyl-1-silapropoxy)phenylamine. (Yield 6.7 g, 97%).

Provenance & Evidence