pyridine; hydrogen; Lindlar's catalyst; α-[2-(2-butoxyethoxy)ethoxy]-4,5-methylenedioxy-2-propyltoluene in methanol

sodium tetrahydroborate in methanol T=0°C;

1: 70 percent / TMEDA, BuLi / tetrahydrofuran; hexane / 1. -20 deg C, 15 min, 2.) r.t., overnight 2: 100 percent / pyridine / 3 h / Ambient temperature 3: 1.) Jones reagent, 2.) AcCl / 1.) acetone, 0 deg C, 2.) r.t., 2 h 4: 99 percent / H2, pyridine / 3.5percent Pb, 5percent Pd/CaCO3 / methanol View Scheme

1: 100 percent / pyridine / 3 h / Ambient temperature 2: 1.) Jones reagent, 2.) AcCl / 1.) acetone, 0 deg C, 2.) r.t., 2 h 3: 99 percent / H2, pyridine / 3.5percent Pb, 5percent Pd/CaCO3 / methanol View Scheme

1: 1.) Jones reagent, 2.) AcCl / 1.) acetone, 0 deg C, 2.) r.t., 2 h 2: 99 percent / H2, pyridine / 3.5percent Pb, 5percent Pd/CaCO3 / methanol View Scheme

1: diethyl ether; methanol 2: NaIO4 / methanol; H2O / 0 °C 3: 25 mg / NaBH4 / methanol / 0 °C View Scheme

1: NaIO4 / methanol; H2O / 0 °C 2: 25 mg / NaBH4 / methanol / 0 °C View Scheme

ethylaluminum dichloride in dichloromethane 2 h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;