Multi-step reaction with 7 steps
1: 1.) KH / 1.) THF, 25 deg C , 2 h, 2.) THF, from 0 deg C to 25 deg C, 1 h
2: aq. H2C2O4 / methanol; tetrahydrofuran / 3 h / 25 °C
3: 1.) CpTi(CH3)2Cl / 1.) THF, Et2O, 25 deg C, 2 h, 2.) THF, Et2O, 25 deg C, 2 h
4: 2.) NaBH3CN / 1.) CH2Cl2, 25 deg C, 2 h, 2.) CH2Cl2, MeOH, 25 deg C, 2 h
5: Mg, CH3OH / 5 h / 25 °C
6: K, t-BuOH, HMPA / diethyl ether; toluene / 4 h / 25 °C
7: H2 / 10percent Pd/C / ethanol / 2068.6 Torr
With
methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; chlorodimethylcyclopentadienyltitanium(IV); hydrogen; oxalic acid; potassium hydride; sodium cyanoborohydride; magnesium; tert-butyl alcohol;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; toluene;