1.1: 5 percent / K2CO3 / dimethylformamide / 120 h / Heating 2.1: NaH / dimethylformamide / 0.33 h 2.2: 20 °C 3.1: aq. KOH / 2 h / Heating View Scheme

potassium carbonate in N,N-dimethyl-formamide T=80°C; 12 h;

potassium hydroxide; tetrabutyl-ammonium chloride T=110°C; 3 h;

2: sodium; alcohol View Scheme

1: 92 percent / K2CO3 / 4-(dimethylamino)pyridine / tetrahydrofuran / 4 h / 23 °C 2: 94 percent / K2CO3 / n-Bu4NI / acetone / 16 h / Heating 3: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating 4: pyridine / tetrahydrofuran / 18 h / 22 °C 5: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C 6: CH2Cl2 / 10 h / 23 °C 7: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 8: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 9: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 10: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 11: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 12: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 13: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 14: tetrahydrofuran / 20 h / 23 °C 15: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 16: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 17: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 18: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 19: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

acetic acid in water T=100°C; 12 h;

in pyridine 1.) 130 deg C to 140 deg C, 3 h 2.) -2 deg C, 12 h;

(heating);

1: acetic acid / 0.5 h / Heating 2: 0.5 h / 160 °C View Scheme

in acetic acid 0.5 h; Heating; Yields of byproduct given;