sodium ethanolate in ethanol 1 h; Heating;

in ethanol T=70°C; 1.5 h;

in methanol 1) 0 deg C, 15 min.; 2) room temp., 1 h; Yield given. Yields of byproduct given;

1: sodium methylate / methanol / 6 h / 80 °C 2: sodium hydroxide / methanol; water / 2 h / 60 °C View Scheme

hydrogenchloride in tetrahydrofuran Ambient temperature;

1: 88 percent / ethanol / 2 h / Heating 2: 85 percent / N-bromosuccinimide / CCl4 / 3 h / Heating; Irradiation 3: 70 percent / sodium ethoxide, 2-nitropropane / ethanol / 2 h / Heating 4: 41 percent / hydroxylamine hydrochloride / ethanol / 16 h / Ambient temperature 5: 61 percent / SOCl2 / diethyl ether / 16 h / Ambient temperature View Scheme

1.1: ethanol / 0.5 h / 45 - 53 °C / |Large scale 2.1: potassium 2-methyl-2-butoxide; ethyl-α,α,α-trifluoroacetate / ethanol; toluene / 9 h / 60 - 63 °C / |Large scale 3.1: sodium hydride / N,N-dimethyl-formamide / |Large scale 4.1: formamide; phosphoric acid / 120 °C 5.1: trichlorophosphate; N-ethyl-N,N-diisopropylamine / toluene / 2 h / 110 °C 6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 58 °C / |Large scale 7.1: sodium hydroxide / water / 6 h / 60 - 65 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 3 h / 20 - 25 °C 8.2: 2 h / 30 - 35 °C View Scheme

1: ethanol / 50 °C 2: ethanol; sodium ethanolate / 60 °C 3: potassium tert-butylate; O-(4-nitrobenzoyl) hydroxylamine / 1-methyl-pyrrolidin-2-one / 25 °C View Scheme

1: acetic acid / 15 h / Ambient temperature 2: acetic acid / 5 h / 70 °C View Scheme

1.1: sodium ethanolate / ethanol / 16 h / |Inert atmosphere 1.2: 0.17 h / |Inert atmosphere 2.1: thionyl chloride / N,N-dimethyl-formamide; toluene / 2 h / 80 °C / |Inert atmosphere View Scheme