1: 83 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.5 h / 20 °C 2: 59 percent / NaOH / ethanol; H2O / 3 h / Heating View Scheme

1: 99 percent / trifluoroacetic anhydride; BF3*Et2O / benzene / 1.5 h / 20 °C 2: 83 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.5 h / 20 °C 3: 59 percent / NaOH / ethanol; H2O / 3 h / Heating View Scheme

1: titanium(IV) isopropoxide / 4 h / 80 °C 2: 25.2 g / NaBH4 / methanol / 1 h / 20 °C 3: 99 percent / 1 h / 60 °C 4: 96 percent / NaIO4 / methanol; H2O / 13 h / 20 °C 5: 99 percent / trifluoroacetic anhydride; BF3*Et2O / benzene / 1.5 h / 20 °C 6: 83 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.5 h / 20 °C 7: 59 percent / NaOH / ethanol; H2O / 3 h / Heating View Scheme

tetrahydrofuran; benzene

1: 1.) NaHCO3, tert-butyl hypochlorite, 2.) KO2, 18-crown-6 ether / 1.) ether, 10 deg C, 2.) ether, 4.5 h View Scheme

1: chlorine 2: aqueous ammonia 3: tetrahydrofuran; benzene View Scheme

1: aqueous ammonia 2: tetrahydrofuran; benzene View Scheme

1: methanol; ammonia 2: tetrahydrofuran; benzene View Scheme

Yield given. Multistep reaction;