Imidazole → HCID 15453718, compound

Participants

Reaction Steps

Add tert-butyl-dimethylsilylchloride (14 g, 90 mmol) to a solution of 4-nitroguaiacol (5 g, 30 mmol) in DMF (250 mL) and then add imidazole (6.13 g, 90 mmol). Stir the mixture at room temperature for 16 h. Quench the reaction mixture with water (150 mL). Extract with diethyl ether (3×200 mL). Wash the combined organic portions with water, brine, and dry over MgSO4. Filter and concentrate to a residue. Purify the residue by silica gel flash chromatography, eluting with 15% ethylacetate:hexanes to give the title compound (8.053 g, 95%) as a pale yellow oil. MS (ES+) 284.1 (M+1)+. 1H NMR (CDCl3): δ 7.79 (dd, J=7.8 Hz, 2.7 Hz, 1H), 7.26 (d, J=2.7 Hz, 1H), 6.69 (d, J=7.8 Hz 1H), 3.85 (s, 3H), 0.96 (s, 9H), 0.18 (s, 6H).

Provenance & Evidence