sulfuric acid Heating;

1: DCCI / ethyl acetate / 4 h 2: NH3 (gas) / CH2Cl2 / 12 h 3: 23 percent / 2 M borane*methyl sulfide complex / tetrahydrofuran / 6 h / Heating View Scheme

1: pyridine / 24 h / Ambient temperature 2: SOCl2, DMF / 1.33 h / Heating 3: 8N NH3/MeOH / diethyl ether / 0.17 h / Ambient temperature 4: SOCl2 / acetonitrile; ethanol / 0.5 h / Heating View Scheme

1: With sodium hydride in N,N-dimethyl-formamide 2: With sodium hydroxide in methanol

1: With dimethylsulfide borane complex in tetrahydrofuran Reflux; 2: With methanol in tetrahydrofuran 3: With acetic acid in tetrahydrofuran; water pH=3;

in tetrahydrofuran; methanol; water; ethyl acetate

1.1: NaH / dimethylformamide 1.2: aq. NaOH / methanol 2.1: N,O-dimethylhydroxylamine hydrochloride; HOBT; EDAC 2.2: 80 percent / DIBAL / tetrahydrofuran / -78 °C View Scheme

1.1: sodium ethanolate / ethyl acetate; ethanol / 0.5 h / |Reflux 1.2: 1 h / |Reflux 2.1: oxalyl dichloride / ethyl acetate; N,N-dimethyl-formamide / 0.5 h / 20 °C / |Large scale 3.1: pyridine / ethyl acetate / 1 h / 20 °C / |Large scale 4.1: camphor-10-sulfonic acid / ethyl acetate / 6 h / |Reflux; |Large scale 4.2: Amberlyst-15 resin / 1 h / |Reflux; |Large scale 5.1: sodium hydroxide / toluene; water / 5 h / 20 °C View Scheme

sodium hydride in toluene 1.) 60 deg C, 2.5 h, 2.) 35 deg C, 72 h; Yield given. Yields of byproduct given;

sodium hydride in N,N,N',N',N'',N''-hexamethylphosphoric triamide 1.) 60 deg C, 2.5 h, 2.) 35 deg C, 4 h; other solvent, other time, other temperatures; Product distribution;