Multi-step reaction with 14 steps
1: 44 percent / SeO2 / aq. ethanol / 9 h / Heating
2: 72 percent / NaBH4 / methanol / 5 h / -10 °C
3: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
4: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
5: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C
6: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
7: 78 percent / dimethylformamide / 24 h / Ambient temperature
8: 1.) n-BuLi, 3.) H2O, KOH
9: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C
10: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature
11: 1.) n-BuLi, 3.) H2O, KOH
12: 70 percent / Li, ethylamine / diethyl ether
13: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C
14: 50 percent / Li, ethylamine / diethyl ether / -78 °C
With
pyridine; potassium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; selenium(IV) oxide; water; phosphorus tribromide; lithium; ethylamine;
In
methanol; diethyl ether; ethanol; N,N-dimethyl-formamide;
DOI:10.1039/P19810000761