diisobutylaluminium hydride in tetrahydrofuran; n-heptane T=-78 - 20°C;

1: 1.) sodium hydride / 1.) dimethoxyethane, room temperature, 25 min, 2.) 2 h, -78 deg C 2: 62 percent / sodium borohydride / methanol / 1 h / 0 °C View Scheme

1: 52 percent / carbontetrabromide, triphenylphosphine / diethyl ether / 1.) 0 deg C, 2.) room temperature, 2 h 2: 35 percent / NaH/t-AmOH/Ni(OAc)2 complex / 1,2-dimethoxy-ethane / 1 h / Ambient temperature View Scheme