Multi-step reaction with 13 steps
2: 73 percent / EtAlCl2 / CH2Cl2; hexane / 4 h / Ambient temperature
3: 34 percent / BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C
4: 95 percent / toluene / 0.75 h / Heating
5: 95 percent / LiAlH4 / diethyl ether / 1.5 h
6: DEAD, Ph3P / diethyl ether / 0.5 h
7: aq. KOH / methanol / 12 h / Ambient temperature
8: 97 percent / H2 / norbornadiene (1,4-bisdiphenylphosphinobutane)rhodium(I) tetrafluoroborate / tetrahydrofuran / 4 h / 46543.3 Torr / Ambient temperature
9: 88 percent / Burgess reagent / benzene / 80 °C
10: 74 percent / Zn-Cu / diethyl ether / 2 h / Ambient temperature
11: 85 percent / Zn-Cu, NH4Cl / methanol / 1.) r.t., 1 h, 2.) reflux, 1 h
12: 73 percent / hexamethyldisilazane, Me3SiI / pentane / 1.) r.t., overnight, 2.) r.t., 30 min
13: 86 percent / LDA / tetrahydrofuran / 1.) r.t., 1 h, 2.) r.t., 30 min
With
potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; Burgess Reagent; trimethylsilyl iodide; hydrogen; ethylaluminum dichloride; copper; ammonium chloride; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; zinc; lithium diisopropyl amide; diethylazodicarboxylate;
[(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; pentane; benzene;
DOI:10.1055/s-1998-5921