Water → Tert-butyl(2-methoxy-5-nitrophenoxy)dimethylsilane

Participants

Reaction Steps

A mixture of 2-methoxy-5-nitrophenol (3.0 g, 17.8 mmol), tert-butyldimethylsilyl chloride (3.2 g, 21.4 mmol), and ethyldiisopropylamine (5.8 g, 44.5 mmol) in DMF (50 mL) was stirred at room temperature for 3 hours. The mixture was poured into water (100 mL) and extracted with methylene chloride (3×100 mL). The combined organic extracts were washed with water (5×100 mL) and dried (MgSO4), and the solvent was evaporated under vacuum. The residue was recrystallized from ethanol-water, providing 3.2 g of the product as white crystals, in 64% yield: 1H NMR (CDCl3) δ 0.19 (s, 6H), 1.01 (s, 9H), 3.91 (s, 3H), 6.89 (d, J=8.9 Hz, 1H), 7.71 (d, J=2.8 Hz, 1H), 7.89 (dd, J=8.9 Hz, J=2.8 Hz, 1H).

Provenance & Evidence