Imidazole → HCID 69516971, compound

Participants

Reaction Steps

A mixture of Example 73B (5.31 g, 20.81 mmol), tert-butyldiphenylsilyl chloride (5.68 mL, 21.85 mmol), imidazole (2.83 g, 41.62 mmol) in anhydrous DMF (100 mL) was heated at 50° C. for 2 days. The solvent was removed via vacuum pump. THF (200 mL) was added. The mixture was ultrosonicated. The suspension was filtered. The solution was dried with silica gel powder (20 g). 20% ethyl acetate in hexanes (1 L) and 30% ethyl acetate in hexanes (1 L) were used to perform flash chromatography to give the title compound (7 g, 68%). MS (APCI) m/z 492.19 (M−H)−; 1H NMR (500 MHz, CDCl3) δ ppm 1.10 (s, 9H) 6.64 (dd, J=8.73, 2.81 Hz, 1 H) 6.78 (d, J=8.73 Hz, 1 H) 6.86 (d, J=2.81 Hz, 1 H) 7.34–7.45 (m, 6 H) 7.70–7.75 (m, 4 H) 7.78 (dd, J=5.46, 2.96 Hz, 2 H) 7.92 (dd, J=5.30, 3.12 Hz, 2 H).

Provenance & Evidence