tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide in dichloromethane T=20°C; 2.08333 h; Inert atmosphereMolecular sieve;

1: NaH 2: SO3*Py; DMSO; Et3N / CH2Cl2 View Scheme

1: NaH 2: SO3*Py; DMSO; Et3N / CH2Cl2 View Scheme

2: LiAlH4 3: PCC View Scheme

1: LiAlH4 2: PCC View Scheme

1.1: LiN(SiMe3)2; HMPA / tetrahydrofuran / 1 h / -40 °C 1.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -78 °C 1.3: 73 percent / methanol; diethyl ether / 0.5 h / 0 °C 2.1: n-Bu4NF / tetrahydrofuran / 3 h / 20 °C 3.1: 90 percent / aq. NaOH / tetrahydrofuran / 20 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C 1.2: 18 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 3.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2 h View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C 1.2: 18 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C View Scheme