sodium hydride in tetrahydrofuran

ruthenium trichloride; sodium periodate in tetrachloromethane; water; acetonitrile 3.5 h; Ambient temperature;

1.1: imidazole / dimethylformamide / 24 h / 20 °C 2.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C 3.1: ICl; NaOAc / tetrahydrofuran; methanol; CH2Cl2 / 0.5 h / 20 °C 4.1: Zn/Cu; BrCH2CH2Br; N,N-dimethyl acetamide / benzene / 2.5 h / 60 °C 4.2: 84 percent / [Pd(PPh3)4] / benzene / 0.5 h / 60 °C 5.1: 82 percent / CSA / CH2Cl2; methanol / 3.5 h / 0 - 20 °C 6.1: 97 percent / pyridine; Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 7.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C 7.2: 85 percent / hexane; tetrahydrofuran / 0.33 h / -78 °C 8.1: 86 percent / PPTS / methanol / 72 h / 20 °C 9.1: 95 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C View Scheme

Yield given. Multistep reaction;

2: 1.) CBr4, Ph3P, 2.) (NH2CH2)2 / 1.) CH2Cl2, room temp., 1 h, 2.) DMSO, 8 deg C View Scheme

1.1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C 2.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C 2.2: 74 percent / K3PO4 / Pd(PPh3)4 / tetrahydrofuran; dioxane / 5 h / 85 °C 3.1: DIBAL-H / diethyl ether; hexane / 0.5 h / -78 °C View Scheme

Swern oxidation;