Multi-step reaction with 7 steps
1: 1.) CuI, 2.) NaCN, NH4Cl, H2O / 1.) Et2O, 20-30 deg C, 30 min, 2.) Et2O, 40 min
2: 91 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -45 deg C, 1 h, 2.) -45 to 20 deg C, 1 h
3: 83 percent / t-BuLi, TMEDA / hexane; tetrahydrofuran / 1.) -70 deg C, 15 min; -70 to 0 deg C, 1 h, 2.) -70 deg C, 15 min; -70 to 20 deg C, 75 min
4: 1.) AgNO3, 2.) KCN / 1.) EtOH, H2O, 0-5 deg C, 15 min, 2.) EtOH, H2O, 20 deg C, 2 h
5: 51 percent / n-BuLi / diethyl ether; hexane / 1.) 0 deg C, 75 min, 2.) 30 min
6: 46 percent / LiAlH4, MeOH / tetrahydrofuran / 5 h / Heating
7: 89 percent / DMAP, Et3N / diethyl ether / 20 °C
With
methanol; dmap; potassium cyanide; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium cyanide; water; tert.-butyl lithium; ammonium chloride; silver nitrate; triethylamine;
In
tetrahydrofuran; diethyl ether; hexane;