in water

in water

1.1: 82 percent / imidazole / dimethylformamide / 20 h / 25 °C 2.1: lithium 2,2,6,6-tetramethylpiperidide / diethyl ether 2.2: diethyl ether 2.3: hydrochloric acid View Scheme

1.1: 2,2,6,6-tetramethylpiperidine; potassium tert-butoxide; N,N,N',N'',N''-pentamethylenediamine / butyllithium / tetrahydrofuran; hexane / 0.75 h / -125 °C 1.2: tetrahydrofuran; hexane 2.1: HCl / H2O 3.1: 1.92 g / NaOH; zinc powder / H2O / 2 h / 25 °C View Scheme

1.1: 88 percent / N-ethyldiisopropylamine / CH2Cl2 / 2 h / 25 °C 2.1: 2,2,6,6-tetramethylpiperidine; potassium tert-butoxide; N,N,N',N'',N''-pentamethylenediamine / butyllithium / tetrahydrofuran; hexane / 0.75 h / -125 °C 2.2: tetrahydrofuran; hexane 3.1: HCl / H2O 4.1: 1.92 g / NaOH; zinc powder / H2O / 2 h / 25 °C View Scheme

1: 1,2,4-trifluoro-3-(methoxymethoxy)benzene With n-butyllithium in tetrahydrofuran 2: carbon dioxide in tetrahydrofuran; hexane 3: With hydrogenchloride in water Title compound not separated from byproducts;

1: triisopropyl(2,3,6-trifluorophenoxy)silane With 2,2,6,6-tetramethylpiperidinyl-lithium in diethyl ether 2: carbon dioxide in diethyl ether 3: With hydrogenchloride Title compound not separated from byproducts;

sodium hydride in N,N-dimethyl-formamide 18 h;

1: 92 percent / NaH / dimethylformamide / 18 h 2: 79 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature View Scheme