4-(N,N-dimethlyamino)pyridine; pivaloyl chloride; N-ethyl-N,N-diisopropylamine in acetonitrile T=45°C; 3 h;

collidine in dichloromethane T=-5 - 0°C; 4 h; Inert atmosphere; Product distribution / selectivity;

1.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 4 h / 20 - 25 °C 2.1: dichloromethane / 4 h / -5 - 30 °C / Inert atmosphere 2.2: 0 - 5 °C View Scheme

1: methanol / Reflux 2: hydrogen / (S)-BINAP RuCl2-triethylamine / methanol / 80 - 85 °C / 4413.43 - 4781.22 Torr 3: sodium hydroxide; water / 65 - 70 °C / Reflux View Scheme

methanol T=60 - 63°C;

in toluene 3 h; Heating;

4-methyl-morpholine in ethyl acetate 6 h; Reflux;

N-ethyl-N,N-diisopropylamine in toluene T=25 - 30°C; Reflux;

in N,N-dimethyl acetamide T=41.1°C; Kinetics; Further Variations:Temperatures;

1: 88.7 percent / toluene / 3 h / Heating 2: 95 percent / ammonium acetate / methanol / 7 h / Heating 3: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr 4: 93 percent / CH2Cl2 / 3 h / 20 °C 5: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C View Scheme