Multi-step reaction with 6 steps
1: 91 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -45 deg C, 1 h, 2.) -45 to 20 deg C, 1 h
2: t-BuLi, TMEDA / hexane; tetrahydrofuran / 1.) -70 deg C, 15 min then; -70 to 0 deg C, 1 h, 2.) -70 deg C, 15 min; -70 to 20 deg C, 75 min
3: 1.) AgNO3, 2.) KCN / 1.) EtOH, H2O, 0-5 deg C, 15 min, 2.) EtOH, H2O, 20 deg C, 2 h
4: 49 percent / n-BuLi / diethyl ether; hexane / 1.) 0 deg C, 75 min, 2.) 30 min
5: 33 percent / LiAlH4, MeOH / tetrahydrofuran / 5 h / Heating
6: 85 percent / DMAP, Et3N / diethyl ether / 20 °C
With
methanol; dmap; potassium cyanide; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; silver nitrate; triethylamine;
In
tetrahydrofuran; diethyl ether; hexane;