1.1: sodium iodide; sodium hydrogencarbonate / 1,1-dimethylpropan-1-ol / 4 h / 75 - 85 °C 2.1: water; sodium carbonate / 1,1-dimethylpropan-1-ol / 16 h / 85 - 88 °C 3.1: sulfuric acid / water; 1,1-dimethylpropan-1-ol / 22 h / 105 °C 3.2: pH 1.5 - 2 4.1: sodium carbonate / sodium iodide / 70 °C View Scheme

formic acid; triethylamine in acetonitrile T=20°C; 24 h; Product distribution / selectivity;

Methylation;

1: With di-isopropyl azodicarboxylate in N,N-dimethyl-formamide T=20 - 55°C; 4 - 42 h; 2: With methanol; dimedone in N,N-dimethyl-formamide T=55 - 60°C; 4 h; Product distribution / selectivity;

1: potassium carbonate / tetrahydrofuran / 1.5 h / 20 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane; tetrahydrofuran / 1 h / 4 °C 3: Burgess Reagent / dichloromethane; tetrahydrofuran / 3 h / -20 - 10 °C 4: ammonia; acetic acid / 18 h / 20 - 50 °C / pH 9 5: triethylamine / 1-methyl-pyrrolidin-2-one; water / 8 h / 70 °C / Inert atmosphere View Scheme