sodium hydride in N,N,N',N',N'',N''-hexamethylphosphoric triamide 1.) 0 degC, 3 h, 2.) 0 degC to R.T., 2.5 h;

1: 93 percent / NaH / tetrahydrofuran / 20 °C 2: KOH / methanol; dioxane / Heating 3: Et3N; PBu3 / tetrahydrofuran / 20 °C 4: 90 percent / n-Bu3SnH; AIBN / benzene / 2 h / Heating View Scheme

1: 90 percent / POCl3 / 4.5 h / 20 - 60 °C 2: NaH / tetrahydrofuran / 0 - 20 °C View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide / 20 °C / Inert atmosphere; Cooling with ice 2.1: sodium hydroxide / ethanol; water / 20 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: thionyl chloride / toluene / 2 h / Inert atmosphere; Reflux 4.1: dichloromethane / 20 °C / Inert atmosphere 5.1: N,N,N',N,-tetramethylethylenediamine; tert.-butyl lithium / tetrahydrofuran / -78 °C / Inert atmosphere 5.2: 20 °C / Inert atmosphere 5.3: 20 °C / Inert atmosphere 6.1: manganese(IV) oxide; acetic acid / dichloromethane / 20 °C / Inert atmosphere 7.1: tetrahydrofuran / -78 °C / Inert atmosphere 7.2: Inert atmosphere 8.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere View Scheme

1: 72 percent / NaOMe / dioxane / 45 h / 110 °C 2: 73 percent / water / aq. NaOH / dioxane / 18 h / 110 °C 3: 83 percent / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 4: 58 percent / BF3*MeOH / 17 h / Ambient temperature View Scheme

1: 69 percent / NaOMe / dioxane / 45 h / 110 °C 2: 94 percent / water / aq. NaOH / dioxane / 17 h / 110 °C 3: 70 percent / PCC / CH2Cl2 / 2 h / Ambient temperature 4: 59 percent / BF3*MeOH / 17 h / Ambient temperature; reaction of its derivatives HCl too with sev. alcohols View Scheme

1.1: 100 percent / DIBAL-H / toluene; tetrahydrofuran / 24 h / -78 °C 2.1: MnO2 / acetonitrile / 24 h 3.1: KHMDS / toluene; tetrahydrofuran / 0.5 h / 20 °C 3.2: 100 percent / toluene; tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: KOH / acetone / 0 - 20 °C 2.1: LiAlH4 / tetrahydrofuran / 0 - 20 °C 3.1: NaH / tetrahydrofuran / 0.5 h / 0 - 20 °C 3.2: 327 mg / tetrahydrofuran / 2 h / 20 °C View Scheme

T=700°C;

methanol; magnesium T=20°C;