sodium tetrahydroborate in ethanol; water 2 h; Ambient temperature;

in diethyl ether 1 h; Heating;

1: 71 percent / n-butyl-lithium, di-isopropylamine / tetrahydrofuran / 1.) -78 deg C, 3.5 h, 2.) room temperature, 18 h 2: 34 percent / diethyl ether / 20 h / Heating 3: 99 percent / sodium borohydride / ethanol; H2O / 2 h / Ambient temperature View Scheme

1: 34 percent / diethyl ether / 20 h / Heating 2: 99 percent / sodium borohydride / ethanol; H2O / 2 h / Ambient temperature View Scheme

1: 75 percent / NaH / tetrahydrofuran / 1.) 2 h, 2.) reflux, dark, 21 h 2: 99 percent / sodium borohydride / ethanol; H2O / 2 h / Ambient temperature View Scheme

toluene-4-sulfonic acid in benzene 0.0833333 h; Heatinglight excluded;

1: 93 percent / toluene-p-sulphonic acid monohydrate / benzene / 0.08 h / Heating; light excluded 2: 98 percent / CCl4 / 6 h / Irradiation; sunlight View Scheme