1: lithium aluminium tetrahydride / diethyl ether / 6 h / 20 °C / |Inert atmosphere 2: Dess-Martin periodane / dichloromethane / 0 °C / |Inert atmosphere 3: Methyltriphenylphosphonium bromide; sodium hydride / tetrahydrofuran; mineral oil / 65 °C / |Inert atmosphere 4: sodium acetate; palladium diacetate / methanol / 12 h / 20 °C / |Inert atmosphere 5: hydrogenchloride / water; methanol / 3 h / 20 - 65 °C / |Inert atmosphere View Scheme

sodium hydride in N,N-dimethyl-formamide T=20°C; 12 h;

N-ethyl-N,N-diisopropylamine in dichloromethane T=0 - 20°C; 12 h; Inert atmosphere;

1: methanol; 3,5-di(hydroxy)benzoic acid With toluene-4-sulfonic acid in hexane Reflux; 2: chloromethyl methyl ether With potassium carbonate in acetone Reflux;

1: HCl / 12 h / 24 °C 2: 1.) NaH / 1.) DMF, 24 deg C, 2.) DMF, 24 deg C, 4 h View Scheme

1: 98 percent / LiAlH4 / diethyl ether / 2 h / 0 - 20 °C 2: 93 percent / N-bromosuccinimide / dimethylformamide / 2 h / 0 °C 3: 95 percent / NaH / dimethylformamide / 1 h / 0 - 20 °C 4: 95 percent / n-BuLi / hexane; diethyl ether / 3 h / -78 - 20 °C 5: 94 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C 6: 72 percent / K2CO3 / acetone / 1 h / 20 °C 7: 90 percent / Cs2CO3 / dimethylformamide / 1 h / 20 °C 8: 86 percent / n-BuLi / tetrahydrofuran; hexane / 3.25 h / -78 - 20 °C 9: 98 percent / Dess-Martin periodinane / CH2Cl2 / 0.75 h / 20 °C 10: 79 percent / H2 / Pd/C / ethanol / 1 h / 20 °C / 760 Torr 11: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 12: aq. NaH2PO4; NaClO2; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol / 1 h / 20 °C 13: 203 mg / diethyl ether; methanol / 0.17 h / 20 °C 14: 81 percent / p-TsOH / methanol / 4 h / Heating View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 2 h; Ambient temperature;

1: LiAlH4 / tetrahydrofuran / 0.5 h 2: PCC, NaOAc / CH2Cl2 / 3 h / 24 °C View Scheme

1: 97 percent / LiAlH4 / tetrahydrofuran / 0 - 18 °C 2: 79 percent / TEA; MsCl / CH2Cl2 / 0 - 18 °C View Scheme