Imidazole → HCID 22270368, compound

Participants

Reaction Steps

To a mixture of 4-(4-chlorophenyl)-2-(3-fluorophenyl)-2-butanol (Step 3, 0.65 g, 2.3 mmol), triphenylphosphine (1.2 g, 4.7 mmol), imidazole (0.32 g, 4.7 mmol) and zinc azide dipyridine complex (Viaud, M. C.; Rollin, P. Synthesis 1990, 130) (0.72 g, 2.3 mmol) in 10 mL of methylene chloride was added diethylazodicarboxylate (0.73 mL, 4.7 mmol) at 0° C. After stirring at room temperature for 30 min, the resulting mixture was concentrated with silica gel (20 g) and loaded onto a silica gel column, which was eluted with 2% ether in hexane to 2% ammonia in methanol (2 M) in 2% ether/hexane to give the title compound. 1H NMR (400 MHz, CD3OD): δ 7.25-6.85 (m, 8H), 3.76 (m, 1H), 3.33 (m, 11H), 2.92 (m, 2H), 1.15 (d, 3H).

Provenance & Evidence