Multi-step reaction with 7 steps
1: 80 percent / 4-N,N-dimethylaminopyridine / CH2Cl2 / 1) room temperature, 1 h; 2) reflux, 6 h
2: 100 percent / m-chloroperbenzoic acid / CH2Cl2 / 1) -10 deg C, 30 min; 2) 0 deg C, 1 h
3: 36 percent / acetic acid, water / 1.75 h / Heating
4: 1.) aq. sodium hydroxide / 1) ethanol, -10 deg C, 5 min; 2) 2 deg C, 80 min
5: molecular sieves / dimethylformamide; toluene / 16 h / 30 °C
6: thionyl chloride, triethylamine / tetrahydrofuran / 0.5 h / 0 °C
7: 2.) aq. sodium carbonate / 1) THF, room temperature, 2 d
With
dmap; sodium hydroxide; thionyl chloride; molecular sieve; water; sodium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00526a045