Multi-step reaction with 9 steps
1: 1.) n-Bu3SnH, 2.) I2 / 1.) 3CN)2> / 1.) THF, 25 deg C, 30 min, 2.) CH2Cl2, 0 deg C, 15 min
2: 62 percent / t-BuLi / diethyl ether; pentane / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1.5 h
3: 86 percent / LiI, LiAlH4 / diethyl ether / 1.) r.t., 30 min, 2.) -100 deg C, 10 min
4: 97 percent / NaH / dimethylformamide / 1.) 25 deg C, 30 min, 2.) 25 deg C, 40 min
5: CSA, MeOH / 3 h / 25 °C
6: Et3N / CH2Cl2 / 0.42 h / 0 °C
7: K2CO3 / methanol / 2 h / 25 °C
8: 1.) t-BuLi, lithium 2-thienylcyanocuprate / 1.) Et2O, pentane, -98 deg C, 30 min; THF, 0 deg C, 5 min, 2.) 0 deg C, 1.5 h
9: 94 percent / 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
With
2,6-dimethylpyridine; methanol; lithium aluminium tetrahydride; camphor-10-sulfonic acid; iodine; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium hydride; potassium carbonate; thien-2-yl(cyano)copper lithium; triethylamine; lithium iodide;
;
In
methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane;