Multi-step reaction with 16 steps
1: NBS, benzoylperoxide / CCl4 / 1 h / Heating
2: CH2Cl2 / Ambient temperature
3: HCl / methanol / 0.67 h / 50 °C
4: BF3-etherate / CH2Cl2 / Ambient temperature
5: conc. HCl / ethanol / 0.75 h / Heating
6: Triton B / CH2Cl2 / 0.5 h / Ambient temperature
7: 97.4 percent / pyridine / 1 h / Ambient temperature
8: TFA / 0.13 h / Ambient temperature
9: Et3N / CH2Cl2 / 0.17 h / Ambient temperature
10: NaBH4 / methanol; CH2Cl2 / 0.17 h / 0 °C
11: Et3N / CH2Cl2 / 0.17 h / Ambient temperature
12: LiCl / dimethylformamide / 0.25 h / Ambient temperature
13: 94 percent / NaOMe / methanol; CH2Cl2 / 0.08 h / Ambient temperature
14: 52.3 percent / phenyllithium / tetrahydrofuran / 0.33 h / -78 °C
15: 59.8 percent / BCl3 / CH2Cl2 / 0.17 h / 0 °C
16: 1.) m-ClPBA; 2.) (CH3)2S, HClO4 / 1.) CH2Cl2, 0 deg C, 10 min 2.) 9 h, r.t.
With
pyridine; hydrogenchloride; sodium tetrahydroborate; N-Bromosuccinimide; perchloric acid; Perbenzoic acid; dimethylsulfide; boron trifluoride diethyl etherate; sodium methylate; boron trichloride; phenyllithium; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium chloride;
N-benzyl-trimethylammonium hydroxide;
In
tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)97960-8