sodium tetrahydroborate in methanol Ambient temperature1.)7 h 2.)r.t., 20 h;

trichloroacetic acid in toluene 17 h; Heating;

1: 1.) n-BuLi / 1.) diethyl ether, hexane, 0 deg C, 30 min, 2.) diethyl ether, hexane, 10 h 2: 17 percent / Cl3CCOOH / toluene / 17 h / Heating View Scheme

1: 90 percent / N-bromosuccinimide (NBS), benzoyl peroxide / CCl4 / 3 h / Heating 2: 83 percent / aq. CaCO3 / dioxane / 10 h / Heating 3: 1.) n-BuLi / 1.) diethyl ether, hexane, 0 deg C, 30 min, 2.) diethyl ether, hexane, 10 h 4: 17 percent / Cl3CCOOH / toluene / 17 h / Heating View Scheme

1: 66.2 percent / AlCl3, NaCl / 3.5 h / 210 - 220 °C 2: NaBH4 / ethanol / 0.75 h / Heating View Scheme

1: 87.6 percent / NaI / dimethylformamide / 16 h / 65 °C 2: 66.2 percent / AlCl3, NaCl / 3.5 h / 210 - 220 °C 3: NaBH4 / ethanol / 0.75 h / Heating View Scheme

1: 66.2 percent / AlCl3, NaCl / 3.5 h / 210 - 220 °C 2: NaBH4 / ethanol / 0.75 h / Heating View Scheme

(i), (ii) NaBH4; Multistep reaction;