Multi-step reaction with 9 steps
1: 85 percent / boron trifluoride etherate / CH2Cl2 / 15 h / Ambient temperature
2: 650 mg / m-chloroperbenzoic acid / CH2Cl2 / 15 h / Ambient temperature
3: 77 percent / dimethylformamide / 15 h / Ambient temperature
4: 1.) H2; 2.) N,N-diisopropylethylamine / 1.) PtO2 / 1.) glacial AcOH, 1 atm, 5 h; 2.) CH2Cl2, roomtemp.
5: 66 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature
6: 90 percent / boron trifluoride etherate / acetonitrile / 0.3 h
7: 66 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 0.5 h
8: triethylamine / benzene / 0.08 h / 40 °C
9: 1.) 2,6-lutidine, thionyl chloride; 2.) 2,6-lutidine / 1.) THF, -20 deg C, 30 min; 2.) dioxane, roomtemp., 3 h then 40 deg C, 13 h
With
2,6-dimethylpyridine; dmap; thionyl chloride; boron trifluoride diethyl etherate; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate;
platinum(IV) oxide;
In
dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1246/bcsj.59.1363