Multi-step reaction with 8 steps
1.1: 100 percent / Et3N; DMAP / CH2Cl2 / 3 h / -78 - 20 °C
2.1: 93 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C
3.1: NaN3 / hexamethylphosphoric acid triamide / 2 h / 40 °C
3.2: 94 percent / TBAF / tetrahydrofuran
4.1: NaH / tetrahydrofuran / 0.5 h / 20 °C
4.2: 97 percent / tetrahydrofuran / 3.5 h / 20 °C
5.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C
6.1: 1.48 g / K2CO3 / dimethylformamide / 1.5 h / 0 - 20 °C
7.1: 90 percent / Et3N / CH2Cl2 / -78 - 20 °C
8.1: 66 percent / Cl2Ru(PCy3)2=CHPh / CH2Cl2 / 52 h / Heating
With
dmap; lithium aluminium tetrahydride; sodium azide; sodium hydride; potassium carbonate; triethylamine;
Grubbs catalyst first generation;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200305581