acetophenone; palladium on activated charcoal in methanol 16 h; Ambient temperature; Product distribution;

ammonium hydroxide; water; sodium hydride; copper dichloride 1.) dimethoxyethane; reflux, 24 h., 2.) cool, dimethoxyethane; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

2,4,6-trichloro-1,3,5-triazine in acetonitrile T=60°C; 0.166667 h; SonicationInert atmosphere; regioselective reaction;

2: 1.) Bu4NF, 2.) PDC / 1.) THF, RT, 18 h, 2.) DMF, RT, 20 h 3: 78 percent / diethyl ether / 0.5 h / 0 °C 4: 68 percent / 48 h / 30 °C / Irradiation 5: 1.) Ac2O, H2SO4, 2.) MeONa / 1.) -20 deg C, 10 min, 2.) methanol, 0 deg C, 10 min 6: 92 percent / Et2NSF3 / CH2Cl2 / 0.17 h / -30 °C 7: 49 percent / toluene / 0.5 h / -20 - 20 °C 8: 1.) pTSA, 2.) Dess-Martin's periodinane / 1.) MeOH, CH2Cl2, RT, 2 h, 2.) CH2Cl2, RT, 30 min 10: LiOH / tetrahydrofuran; H2O / 18 h / Ambient temperature 11: Li, liq. NH3 / ethanol / 0.5 h / -78 °C View Scheme