1: 1.) HBr, 2.) KOH / 1.) glacial acetic acid, 0 deg C, 5 min, 2.) methanol, 15 min 2: 1.) BuLi, 2.) BF3*Et2O / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 1.5 h 3: H2 / Lindlar cat. / ethyl acetate 4: p-toluenesulfonic acid hydrate / toluene; H2O / 1 h / Heating View Scheme

potassium hydroxide; hydrogen bromide 1.) glacial acetic acid, 0 deg C, 5 min, 2.) methanol, 15 min; Yield given. Multistep reaction;

Multi-step reaction with 3 steps 1: 18 mg / SnCl4 / CH2Cl2 / 48 h / -78 °C2: 87 percent / H2 / 10percent Pd/C / ethyl acetate / 3 h / 20 °C3: 1.) LAH, 2.) sodium potassium tartrate / 1.) Et2O, RT, 3 h, 2.) Et2O, 2 h