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Reagent and conditions: (a) Conc. H2SO4, MeOH, 0°C to rt, 6 hrs. (b) Triethylamine(1.5 equiv.), THF, 0°C - r.t., 4 hrs. (c) SnCl2 (3.0 equiv.), ethanol, reflux, 2 hrs, (d) NaNO2(aq), HCl-AcOH, 0°C, 0.5 hrs. (e) Cu powder, 70°C. (f) Lithium hydroxide (1.5 equiv.), MeOH-water (5∶1), 0°C to rt, 1.5 hrs. (g) EDC.HCl (1.5 equiv.), HOBT (1.2 equiv.), TEA (3 equiv.), 0°C to rt, 7.0 hrs. (h) 4(M) HCl in 1,4 dioxane, 0°C to rt, 2.0 hrs.
