jones reagent in acetone 0.333333 h; Yield given;

1: 9.15 g / diisopropylethylamine / CH2Cl2 / 2 h 2: 13.61 g / imidazole / dimethylformamide / 6 h 3: 12.40 g / LiBH4 / tetrahydrofuran / 1.5 h / 35 °C 4: 68 percent / PPh3, diisopropylazodicarboxylate / tetrahydrofuran; acetonitrile / 24 h / Ambient temperature 5: CuCN / tetrahydrofuran; diethyl ether / 1 h / -40 °C 6: Bu4NF / tetrahydrofuran / 1 h / 4 °C 7: Jones reagent / acetone / 0.33 h View Scheme

1: 13.61 g / imidazole / dimethylformamide / 6 h 2: 12.40 g / LiBH4 / tetrahydrofuran / 1.5 h / 35 °C 3: 68 percent / PPh3, diisopropylazodicarboxylate / tetrahydrofuran; acetonitrile / 24 h / Ambient temperature 4: CuCN / tetrahydrofuran; diethyl ether / 1 h / -40 °C 5: Bu4NF / tetrahydrofuran / 1 h / 4 °C 6: Jones reagent / acetone / 0.33 h View Scheme

1: 12.40 g / LiBH4 / tetrahydrofuran / 1.5 h / 35 °C 2: 68 percent / PPh3, diisopropylazodicarboxylate / tetrahydrofuran; acetonitrile / 24 h / Ambient temperature 3: CuCN / tetrahydrofuran; diethyl ether / 1 h / -40 °C 4: Bu4NF / tetrahydrofuran / 1 h / 4 °C 5: Jones reagent / acetone / 0.33 h View Scheme

1: 68 percent / PPh3, diisopropylazodicarboxylate / tetrahydrofuran; acetonitrile / 24 h / Ambient temperature 2: CuCN / tetrahydrofuran; diethyl ether / 1 h / -40 °C 3: Bu4NF / tetrahydrofuran / 1 h / 4 °C 4: Jones reagent / acetone / 0.33 h View Scheme

1: CuCN / tetrahydrofuran; diethyl ether / 1 h / -40 °C 2: Bu4NF / tetrahydrofuran / 1 h / 4 °C 3: Jones reagent / acetone / 0.33 h View Scheme

jones reagent; hydrogen; palladium on activated charcoal 1.) acetone, 0 deg C, 2 h, 2.) CH3OH, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

1: Jones reagent 2: H2 View Scheme

hydrogen Yield given. Yields of byproduct given;