4-fluorophenyl boronic acid; potassium carbonate in N,N-dimethyl-formamide T=20°C; 38 h;

potassium tert-butylate in 1,4-dioxane T=90°C; 2 h;

lithium aluminium tetrahydride; aluminium trichloride in diethyl ether; dichloromethane Heating;

1: TsOH*H2O / benzene / Heating 2: DIBAL / CH2Cl2 View Scheme

1: TsOH*H2O / benzene / Heating 2: DIBAL / CH2Cl2 View Scheme

1: 99 percent / camphorsulfonic acid; molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h 2: 93 percent / lithium aluminum hydride; aluminum chloride / diethyl ether; CH2Cl2 View Scheme

lithium borohydride in tetrahydrofuran

1: diethyl ether 2: lithium borohydride / tetrahydrofuran View Scheme

Swern Oxidation;

1: 93 percent / 1 h / -78 - 0 °C 2: 93 percent / NaH / toluene; tetrahydrofuran / 1 h / 0 - 20 °C 3: 99 percent / DIBAl-H / diethyl ether / 3 h / 0 - 20 °C 4: 96 percent / tBuOOH; Ti(OiPr)4; (-)-diethyl tartrate / CH2Cl2 / -40 - 20 °C 5: 96 percent / Red-Al / tetrahydrofuran / 1 h / 0 °C 6: 98 percent / imidazole / dimethylformamide / 44 h / 60 °C 7: 80 percent / H2 / Pd/C / ethanol / 48 h / 20 °C 8: 97 percent / 1 h / -78 - 0 °C 9: 82 percent / diethyl ether / 0.5 h / 0 °C 10: 80 percent / CrO3; H2SO4 / acetic acid / 2 h View Scheme