lithium aluminium tetrahydride in diethyl ether 1 h; Inert atmosphere;

1: diethyl ether 2: LiAlH4 View Scheme

1: 1.) BuLi 2: diethyl ether 3: LiAlH4 View Scheme

1: 58 percent / dimethylaminopyridine / 1 h / Ambient temperature 2: 95 percent / 1.2 N diisobutylaluminiumhydride / hexane; toluene / 1 h / 0 °C View Scheme

1: 1.) KOH / 1.) water, 15 min; 2.) DMF, 24 h, r.t. 2: 58 percent / dimethylaminopyridine / 1 h / Ambient temperature 3: 95 percent / 1.2 N diisobutylaluminiumhydride / hexane; toluene / 1 h / 0 °C View Scheme

1: 85 percent / PCC / CH2Cl2 / 8 h / 70 °C 2: 1.) 12N KOH / 1.) 15 min, reflux 2.) DMF, room temp., 24 h. 3: DMAP, Et3N / CH2Cl2 4: DIBAH / toluene / 1 h / 0 °C View Scheme

1: 56 percent / 8 N Jones reagent / acetone / 5 h / Ambient temperature 2: 30 percent / conc. sulfuric acid / acetic acid / 8 h / Heating 3: 1.) KOH / 1.) water, 15 min; 2.) DMF, 24 h, r.t. 4: 58 percent / dimethylaminopyridine / 1 h / Ambient temperature 5: 95 percent / 1.2 N diisobutylaluminiumhydride / hexane; toluene / 1 h / 0 °C View Scheme

1: 30 percent / conc. sulfuric acid / acetic acid / 8 h / Heating 2: 1.) KOH / 1.) water, 15 min; 2.) DMF, 24 h, r.t. 3: 58 percent / dimethylaminopyridine / 1 h / Ambient temperature 4: 95 percent / 1.2 N diisobutylaluminiumhydride / hexane; toluene / 1 h / 0 °C View Scheme

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere 1.2: 3.17 h / -78 - 20 °C / Inert atmosphere 2.1: copper(l) iodide / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C / Inert atmosphere 2.2: 1 h / -78 °C / Inert atmosphere 3.1: lithium aluminium tetrahydride / diethyl ether / 1 h / Inert atmosphere View Scheme

1.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere 2.2: 3.17 h / -78 - 20 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C / Inert atmosphere 3.2: 1 h / -78 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / diethyl ether / 1 h / Inert atmosphere View Scheme