diisobutylaluminium hydride in hexane; toluene 1 h; Ambient temperature;

1: 2.) 48percent HBr / 1.) acetone, reflux, 12 h, 2.) MeOH, reflux, 2 h 2: 72 percent / dimethylformamide / 48 h / Heating 3: 1.) DIBAL, 2.) 10percent H2SO4, MeOH / 1.) toluene, RT, 3 h, 2.) toluene, RT, 40 min, overnight View Scheme

1: 2.) 48percent HBr / 1.) acetone, reflux, 12 h, 2.) MeOH, reflux, 2 h 2: 72 percent / dimethylformamide / 48 h / Heating 3: 1.) DIBAL, 2.) 10percent H2SO4, MeOH / 1.) toluene, RT, 3 h, 2.) toluene, RT, 40 min, overnight View Scheme

1: 56 percent / dimethylformamide / 24 h / Heating 2: 60 percent / sodium hypophosphite hydrate / Ra-Ni / H2O; acetic acid; pyridine / 7 h / 100 °C View Scheme

1: 2)HBr / 1) acetone, reflux, 3 h, 2) methanol, reflux, 60 min 2: 56 percent / dimethylformamide / 24 h / Heating 3: 60 percent / sodium hypophosphite hydrate / Ra-Ni / H2O; acetic acid; pyridine / 7 h / 100 °C View Scheme

n-butyllithium; N,N,N',N,-tetramethylethylenediamine 1.) toluene, hexane, -78 deg C to -20 deg C, 2.) toluene, hexane, form -20 deg C to RT; Yield given. Multistep reaction;