Multi-step reaction with 12 steps
1.1: 20 percent / trifluoroacetic acid; aq. tert-butyl hydroperoxide; FeSO4*7H2O / acetonitrile / 4 h / Heating
2.1: potassium tert-butoxide / tetrahydrofuran / 0.17 h / 20 °C
2.2: tetrahydrofuran / 16 h
2.3: 77 percent / ammonium acetate; acetic acid / tetrahydrofuran / 4 h / Heating
3.1: potassium tert-butoxide / dimethylformamide / 1 h / 20 °C
3.2: 82 percent / O2 / dimethylformamide / 6 h
4.1: 77 percent / SOCl2 / 24 h / Heating
5.1: 87 percent / NaBH4 / tetrahydrofuran; ethanol / 8 h / 0 - 80 °C
6.1: 98 percent / NaH / dimethylformamide / 20 °C
7.1: 83 percent / 3-chloroperoxybenzoic acid / CH2Cl2 / 12 h / 20 °C
8.1: 98 percent / Bu4NF / tetrahydrofuran / 3 h / 20 °C
9.1: 91 percent / pyridine; 4-(dimethylamino)pyridine / 30 h / 20 °C
10.1: 89 percent / dimethylformamide / 14 h / 100 °C
11.1: aq. NaOH / methanol; ethane-1,2-diol / 6 h / Heating
12.1: 290 mg / dimethylformamide / 3 h / 20 °C
With
pyridine; tert.-butylhydroperoxide; dmap; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; iron(II) sulfate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethylene glycol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja048537q