in methanol T=0°C; 4 h;

18 h; Amberlyst 15 ion exchange resin; Yield given;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in toluene 3 h; Heating;

1: 95.9 percent / HC(OCH3)3, p-TsOH / 3 h / 100 - 110 °C 2: 1.) LiOCH3; 2.) Na2B2O7, KMnO4 / 1.) CH3OH, 0 deg C, 15 min; 2.) H2O, 0 deg C, 30 min. 3: 96.4 percent / KOH, hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 5.5 h / Heating View Scheme