Multi-step reaction with 8 steps
1: 73 percent / NaH, Bu4NI / tetrahydrofuran / 0.5 h / Heating
2: 89 percent / BuLi / toluene / 24 h / -20 °C
3: 53 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, molecular sieves (4 Angstroem) / CH2Cl2 / 4 h / 22 °C
4: 81 percent / iBu2AlH / CH2Cl2 / 2 h / -78 °C
5: 98 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / 2 h / -78 °C
6: 1.) Mg / 2.) THF, 22 deg C, 6 h
7: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 22 °C
8: 1.) Cp2TiCl2 / 2.) THF, 22 deg C, 1 h
With
bis(cyclopentadienyl)titanium dichloride; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; dichloromethane; toluene;