triethylamine; sodium iodide; magnesium chloride in acetonitrile T=25°C; 3 h;

hydrogenchloride

phosphate buffer in dimethyl sulfoxide T=20°C; pH=7.43; 1 h; Enzyme kinetics;

1.1: 92 percent / Ac2O; H2SO4 / 12 h / 0 °C 2.1: LDA / pentane; tetrahydrofuran / -78 °C 2.2: pentane; tetrahydrofuran / 0.33 h 2.3: TFA / pentane; tetrahydrofuran / 0.17 h / -78 °C 3.1: 4.00 g / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C View Scheme

1.1: 92 percent / Ac2O; H2SO4 / 12 h / 0 °C 2.1: LDA / pentane; tetrahydrofuran / -78 °C 2.2: pentane; tetrahydrofuran / 0.33 h 2.3: TFA / pentane; tetrahydrofuran / 0.17 h / -78 °C View Scheme

1.1: 92 percent / Ac2O; H2SO4 / 12 h / 0 °C 2.1: LDA / pentane; tetrahydrofuran / -78 °C 2.2: pentane; tetrahydrofuran / 0.33 h 2.3: TFA / pentane; tetrahydrofuran / 0.17 h / -78 °C 3.1: 4.00 g / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 4.1: 83 percent / sodium methoxide / methanol / 0 °C View Scheme

1.1: 92 percent / Ac2O; H2SO4 / 12 h / 0 °C 2.1: LDA / pentane; tetrahydrofuran / -78 °C 2.2: pentane; tetrahydrofuran / 0.33 h 2.3: TFA / pentane; tetrahydrofuran / 0.17 h / -78 °C 3.1: 4.00 g / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 4.1: 83 percent / sodium methoxide / methanol / 0 °C 5.1: 93 percent / CH2Cl2 / 2 h / 20 °C View Scheme