Multi-step reaction with 8 steps
1: 98 percent / 4-(dimethylamino)pyridine / pyridine / Ambient temperature
2: 50 percent / LiCl, Pd(PPh3)4 / tetrahydrofuran / Ambient temperature
3: 84 percent / NaH / tetrahydrofuran
4: 1.) m-chloroperbenzoic acid, 2.) HBF4 / 1.) CH2Cl2, 2.) CH2Cl2, room temp.
5: 74 percent / CeCl3 / tetrahydrofuran
6: SOCl2, pyridine / tetrahydrofuran / 1 h / Ambient temperature
7: NaH / dimethylformamide / 6 h / Ambient temperature
8: 91 percent / m-chloroperbenzoic acid, NaHCO3 / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) -78 C to 0 deg C, 1 h
With
pyridine; dmap; tetrafluoroboric acid; tetrakis(triphenylphosphine) palladium(0); thionyl chloride; cerium(III) chloride; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; lithium chloride;
In
tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo971377z