Multi-step reaction with 13 steps
1: dimethylformamide / 20 °C
2: 1.) O3, 2.) (CH3O)3P / 1.) CH2Cl2/MeOH, -78 deg C, 2.) 25 deg C, overnight
3: 96.7 percent / NaCNBH3, sodium acetate / methanol / 24 h / 25 °C
4: 80percent m-chloroperbenzoic acid / CH2Cl2 / 1 h / 0 °C
5: dimethylsulfoxide; benzene / Heating; the benzene, water, and dimethylhydroxylamine was distilled off
6: 90.6 percent / TsOH / benzene / 20 h / Heating; by azeotropic removal of water
7: NaOH / ethane-1,2-diol; H2O; methanol / 75 h / 110 °C / the methanol was distilled off
8: ethane-1,2-diol; H2O; dimethylformamide / 25 °C
9: 1.) O3, 2.) (CH3O)3P / 1.) CH2Cl2/MeOH, -78 deg C, 1 h, 2.) 25 deg C, overnight
10: 96 percent / HONH2*HCl / pyridine / 1.) 0 deg C, 1 h, 2.) 25 deg C, overnight
11: 100 percent / N-chlorosuccinimide / dimethylformamide / 1 h / 40 °C / (cooling !)
12: 76 percent / triethylamine / diethyl ether / 0.5 h / 25 °C
13: 70 percent / CH2Cl2 / 24 h / 25 °C
With
sodium hydroxide; N-chloro-succinimide; hydroxylamine hydrochloride; sodium acetate; sodium cyanoborohydride; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; phosphorous acid trimethyl ester;
toluene-4-sulfonic acid;
In
pyridine; methanol; diethyl ether; dichloromethane; water; ethylene glycol; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00265a033