1: 100 percent / H2 / 10 percent Pd/C / ethyl acetate / 1 h / 2068.59 Torr 2: 62 percent / cerrium ammonium nitrate; H2O / acetonitrile / 0.5 h / 0 - 5 °C View Scheme

1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 1 h / 1034.32 Torr / Inert atmosphere; Autoclave 2: ammonium cerium (IV) nitrate / ethylene glycol dimethyl ether; water / 8 h / 20 °C / Inert atmosphere View Scheme

hydrogen; palladium on activated charcoal in ethyl acetate Catalytic hydrogenation; P=2068.59 Torr; 1 h;

3,4,5-trimethoxyphenylboronic acid in acetic acid; toluene Cyclization; 4 h; Heating;

1: 5-bromo-6-methoxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.5 h; 2: methyl chloroformate in tetrahydrofuran; hexane T=-78°C; 2 h;

in various solvent(s) 0.0166667 h; Irradiation;

hydrogenchloride in methanol T=65°C; 0.5 h; Yield given;

1: With aniline in toluene T=60°C; 24 h; Inert atmosphere; 2: With FeCl3*DMF in diethyl ether; water

1.1: 35 percent / AgNO3; ammonium persulfate / acetonitrile; H2O / 6 h / 65 - 70 °C 2.1: m-chloroperbenzoic acid / CH2Cl2 / 16 h / 20 °C 3.1: sodium dithionite / diethyl ether; H2O / 0.5 h / 20 °C 3.2: 1.26 g / acetic acid; sulfuric acid / H2O / 6 h / 20 °C 4.1: 90 percent / K2CO3 / acetone / 3 h / Heating 5.1: 95 percent / N-bromosuccinimide / CH2Cl2 / 0.17 h / 20 °C 6.1: pyridine / 16 h / 20 °C 7.1: 73 percent / KOtBu / tetrahydrofuran / 6 h / 20 °C 8.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 8.2: 8 percent / tetrahydrofuran; hexane / 2 h / -78 °C View Scheme

1.1: sodium dithionite / diethyl ether; H2O / 0.5 h / 20 °C 1.2: 1.26 g / acetic acid; sulfuric acid / H2O / 6 h / 20 °C 2.1: 90 percent / K2CO3 / acetone / 3 h / Heating 3.1: 95 percent / N-bromosuccinimide / CH2Cl2 / 0.17 h / 20 °C 4.1: pyridine / 16 h / 20 °C 5.1: 73 percent / KOtBu / tetrahydrofuran / 6 h / 20 °C 6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.2: 8 percent / tetrahydrofuran; hexane / 2 h / -78 °C View Scheme