n-butyllithium in tetrahydrofuran; hexane; water

sodium hydroxide in methanol 2 h; Heating;

1: 95.5 percent / K2CO3, tetra-n-butylammonium chloride / acetonitrile / 22 h / Heating 2: 94.9 percent / N-methylpyrrolidone / 1.5 h / Heating 3: OsO4 / diethyl ether; H2O / 0.17 h / 20 - 25 °C 4: NaIO4 / diethyl ether; H2O / 12 h / 20 - 25 °C 5: NaBH4 / methanol / 2 h / 20 - 25 °C 6: 86.7 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 1 h / 20 - 25 °C 7: NCS / dimethylformamide / 3 h / 70 °C 8: 90.3 percent / 4N NaOH / methanol / 2 h / Heating View Scheme

1: 94.9 percent / N-methylpyrrolidone / 1.5 h / Heating 2: OsO4 / diethyl ether; H2O / 0.17 h / 20 - 25 °C 3: NaIO4 / diethyl ether; H2O / 12 h / 20 - 25 °C 4: NaBH4 / methanol / 2 h / 20 - 25 °C 5: 86.7 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 1 h / 20 - 25 °C 6: NCS / dimethylformamide / 3 h / 70 °C 7: 90.3 percent / 4N NaOH / methanol / 2 h / Heating View Scheme

1: OsO4 / diethyl ether; H2O / 0.17 h / 20 - 25 °C 2: NaIO4 / diethyl ether; H2O / 12 h / 20 - 25 °C 3: NaBH4 / methanol / 2 h / 20 - 25 °C 4: 86.7 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 1 h / 20 - 25 °C 5: NCS / dimethylformamide / 3 h / 70 °C 6: 90.3 percent / 4N NaOH / methanol / 2 h / Heating View Scheme

1: NaBH4 / methanol / 2 h / 20 - 25 °C 2: 86.7 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 1 h / 20 - 25 °C 3: NCS / dimethylformamide / 3 h / 70 °C 4: 90.3 percent / 4N NaOH / methanol / 2 h / Heating View Scheme

1: 86.7 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 1 h / 20 - 25 °C 2: NCS / dimethylformamide / 3 h / 70 °C 3: 90.3 percent / 4N NaOH / methanol / 2 h / Heating View Scheme

1: NCS / dimethylformamide / 3 h / 70 °C 2: 90.3 percent / 4N NaOH / methanol / 2 h / Heating View Scheme