Imidazole → HCID 66642939, compound

Participants

Reaction Steps

A solution of 4-amino-3,5-dimethylphenol (5.0 g, 36.46 mmol, Fieser, L. F. Organic Syntheses, Collect Vol II, 1943, 39), imidazole (6.21 g, 77.37 mmol) and triisopropylsilyl chloride (7.70 g, 40.1 mmol) in CH2Cl2 (80 mL) was stirred at room temperature for 1 h. The reaction mixture was diluted with CH2Cl2 (100.0 mL) and washed with water and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:19) to afford 2,6-dimethyl-4-triisopropylsilanyloxyphenylamine (8.46 g, 79%): 1H NMR (300 MHz, CDCl3): δ 6.57 (s, 2 H), 2.19 (s, 6 H), 1.23 (m, 3 H), 1.12 (m, 18 H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:9); Rf=0.51.

Provenance & Evidence