1: ethyl bromide With magnesium Metallation; 2: 3-phenylmethyloxybenzaldehyde in diethyl ether T=20°C; Grignard reaction;

diethyl ether

in ethanol; water T=80°C; 0.0833333 h;

(i) Ph3P, DMF, (ii) /BRN= 1956589/, NaOEt, EtOH, (iii) H2, Pd-C; Multistep reaction;

1.1: potassium carbonate / 1,4-dioxane / 16 h / Reflux 2.1: (C5H3N)(MeC=N(C6H4-2,6-iPr2))2; ethylmagnesium bromide; iron(II) chloride / tetrahydrofuran; diethyl ether / 2 h / 20 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere View Scheme

1: acetic anhydride; sodium acetate / 3.5 h / 115 °C / |Inert atmosphere 2: hydrogen; palladium 10 on activated carbon / methanol / 4 h / 825.08 Torr View Scheme

sodium hydroxide

1.1: sodium dihydrogenphosphate; dihydrogen peroxide; sodium chlorite / water; acetonitrile / 1.5 h / 10 - 20 °C 1.2: 0.08 h 2.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 20 °C View Scheme

1: 1.) Mg / 1.) THF, 2.) THF, 24 h 2: 81 percent / toluene-4-sulphonic acid / ethanol / 24 h / Heating 3: 1.) KOH, 2.) H2, H2SO4 / 2.) 10percent Pd/C / 1.) ethanol, 1 h, reflux, 2.) ethanol, r.t. 4: 4.31 g / PBr3 / CHCl3 / 4 h / 0 °C 5: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 6: p-TsOH / ethanol / 3 h / Heating 7: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 8: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 9: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme