toluene-4-sulfonic acid 6 h; Heating; Further byproducts given;

1: H+ 2: H2 / 10 percent Pd/C 3: LiAlH4 View Scheme

alkali

1.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 20 °C / 760.05 Torr / Inert atmosphere 2.1: potassium carbonate / acetone / Inert atmosphere; Reflux 3.1: water; potassium hydroxide / methanol / 70 °C 4.1: triethylamine / tetrahydrofuran / -70 - 0 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran; hexane / -70 °C / Inert atmosphere 5.2: -70 - 0 °C / Inert atmosphere 6.1: potassium hexamethylsilazane / tetrahydrofuran; hexane / 1.17 h / -72 °C / Inert atmosphere 6.2: 2 h / -72 °C / Inert atmosphere 7.1: lithium borohydride / methanol; diethyl ether / 20 °C 8.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 20 °C 9.1: Fetizon's reagent (silver carbonate on celite) / benzene / 4 h / Reflux 10.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere 10.2: 22 h / -78 - -50 °C / Inert atmosphere 11.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 20 °C / 760.05 Torr / Inert atmosphere 12.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / -15 °C View Scheme

salcomine; oxygen 1.) methanol, 25 deg C, 10 atm, 72 h, 2.) methanol, ether; Yield given. Multistep reaction. Yields of byproduct given;

1: 85 percent / DMAP, pyridine / 4.5 h / 23 °C 2: oxalyl chloride, DMF / CH2Cl2 / 3.5 h / 0 - 23 °C 3: 50 percent / DMAP, pyridine / 24 h / 23 °C 4: 29 percent / NH3 / methanol / 0.5 h / 23 °C View Scheme

1: diethylcyanophosphonate; Et3N / dimethylformamide / 20 h / 20 °C 2: KOH / methanol / 0.5 h / 100 °C View Scheme

1: 100 percent / H2 / 5percent Pd(C) / ethyl acetate / 760 Torr 2: KI, K2CO3 / acetone / 48 h / Heating 3: 20percent aq. NaOH / acetone / 48 h / Heating 4: 1.)LDA, 2.) I2 / 1.) THF, from -78 deg C to RT, 5 h, 2.) THF, from -78 deg C to RT, 18 h 5: Ac2O / 24 h / Heating 6: 24 h / 80 °C 7: 1.) BH3*THF, 2) aq. HCl / 1.) THF, from -17 deg C to RT, 185 min, 2.)0 degC, 1h View Scheme

Microwave irradiation;

T=25°C; Kinetics;