Imidazole → HCID 57036210, compound

Participants

Reaction Steps

The crude compound (1) was dissolved in N,N-dimethylformamide (150 mL) and treated at room temperature with imidazole (44.8 g, 658 mmol) and t-butyldiphenylsilyl chloride (85.6 mL, 329 mmol). The resulting solution was stirred at room temperature for 2 d (reaction was essentially complete after a few hours) after which time it was diluted with 10% ethyl acetate in hexane, washed 3× with water, dried over anhydrous MgSO4, filtered and evaporated to give crude 1-methoxy-4-[2-(t-butyldiphenylsilyl)hydroxyethyl]-cyclohexa-1,4-diene (3). The mixture, which was contaminated with the over-reduced product 4-[2-(t-butyldiphenylsilyl)hydroxyethyl]-cyclohex-1-ene (4), was used in the next step without further purification. Compound (3): 1H NMR (CDCl3) δ 1.07 (9H, s), 2.25 (2H, t, J=6.0 Hz), 2.70 (4H, s), 3.55 (3H, s), 3.77 (2H, t, J=6.0 Hz), 4.62 (1H, br s), 5.43 (1H, br s), 7.22-7.93 (10H, m).

Provenance & Evidence