sodium hydroxide in tetrahydrofuran; water T=20°C; Inert atmosphere;

triethylamine; triphenylphosphine; palladium diacetate in acetonitrile T=110 - 115°C; 16 h;

sodium hydroxide in methanol 1.5 h; Heating;

sodium methylate in methanol

sodium hydroxide in methanol 0.166667 h; Heating;

sodium hydroxide in methanol 18 h; Heating;

1: 93 percent / NaH 2: 73 percent / H2 / 20percent Pd(OH)2-C 3: 1.) NaNO2, hydrogen chloride, 2.) KI 4: 99 percent / NaOMe / methanol View Scheme

1: 73 percent / H2 / 20percent Pd(OH)2-C 2: 1.) NaNO2, hydrogen chloride, 2.) KI 3: 99 percent / NaOMe / methanol View Scheme

1: 87.3 percent / triethylamine, ethyl bromoacetate / methanol / 92.5 h / Ambient temperature 2: 95.1 percent / NaH(50percent) / dimethylformamide / 4 h 3: 92.5 percent / titanium(III) chloride / methanol; H2O / 0.12 h / Ambient temperature 4: 1.) NaNO2, HCl (2N) 2.) CuCl, HCl / 1.) water, 5 deg C, 20 min, 2.) water, room temp., 30 min; 97 deg C, 5 min 5: 92.7 percent / aq. NaOH (40percent) / methanol / 0.17 h / Heating View Scheme

1: 1.) NaNO2, hydrogen chloride, 2.) KI 2: 99 percent / NaOMe / methanol View Scheme