hydrogenchloride in tetrahydrofuran; water T=20°C; 2 h;

1: 87 percent / imidazole / dimethylformamide / 20 h / 20 °C 2: 67 percent / KMnO4; NaOH / 2-methyl-propan-2-ol; H2O / 0.33 h / 0 °C 3: 48 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -60 - 20 °C 4: 88 percent / HCl / H2O; tetrahydrofuran / 2 h / 20 °C View Scheme

1: HCl / 24 h / 20 °C 2: 0.94 g / LiAlH4 / diethyl ether / 1 h / 0 °C 3: 87 percent / imidazole / dimethylformamide / 20 h / 20 °C 4: 67 percent / KMnO4; NaOH / 2-methyl-propan-2-ol; H2O / 0.33 h / 0 °C 5: 48 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -60 - 20 °C 6: 88 percent / HCl / H2O; tetrahydrofuran / 2 h / 20 °C View Scheme

1: 0.94 g / LiAlH4 / diethyl ether / 1 h / 0 °C 2: 87 percent / imidazole / dimethylformamide / 20 h / 20 °C 3: 67 percent / KMnO4; NaOH / 2-methyl-propan-2-ol; H2O / 0.33 h / 0 °C 4: 48 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -60 - 20 °C 5: 88 percent / HCl / H2O; tetrahydrofuran / 2 h / 20 °C View Scheme

1: 67 percent / KMnO4; NaOH / 2-methyl-propan-2-ol; H2O / 0.33 h / 0 °C 2: 48 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -60 - 20 °C 3: 88 percent / HCl / H2O; tetrahydrofuran / 2 h / 20 °C View Scheme

1: 48 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -60 - 20 °C 2: 88 percent / HCl / H2O; tetrahydrofuran / 2 h / 20 °C View Scheme