Multi-step reaction with 8 steps
1: 88 percent / SF6, HF (gas) / 8 h / 120 °C
2: 1.) n-BuLi / 1.) Et2O, hexane, -78 deg C, 5 min, 2.) Et2O, hexane, -78 deg C
3: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature
4: 1.) isopropylmagnesium chloride / 1.) THF, -78 deg C, 20 min, 2.) THF, from -78 deg C to 5 deg C
5: 1.) acetic anhydride / 1.) reflux, 36 h, 2.) DMSO, RT, 50 h
6: triethylamine / dimethylsulfoxide / 40 h / 25 °C
7: 81 percent / 5.0 M aq. HCl / tetrahydrofuran / 1.) RT, 22 h, 2.) reflux, 5 h
8: 80 percent / triethylamine / acetonitrile / 2 h / Heating
With
hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen fluoride; isopropylmagnesium chloride; acetic anhydride; triethylamine; N,N-dimethyl-formamide; sulfur(VI) hexafluoride;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetonitrile;
DOI:10.1021/jm00080a023