Multi-step reaction with 18 steps
1: 99.3 percent / pyridinium p-toluenesulfonate / CH2Cl2; tetrahydrofuran / 14 h / Ambient temperature
2: 1.) borane, 2.) aq. NaOH, 30percent H2O2 / 1.) THF, RT, 14 h, 2.) RT, 4 h
3: 90 percent / chromium oxide, pyridine / 14 h / Ambient temperature
4: 91 percent / pyridinium p-toluenesulfonate / CHCl3; methanol / 2 h / Heating
5: 95 percent / pyridine / 14 h / Ambient temperature
6: 83.8 percent / HBr, Br2 / acetic acid / 3 h / 50 °C
7: 44.5 percent / lithium bromide monohydrate, lithium carbonate / dimethylformamide / 3 h / 150 °C
8: 90 percent / selenium dioxide / dioxane / 0.5 h / 50 °C
9: 90 percent / 5percent aq. KOH / methanol / 1 h / Ambient temperature
10: 99.9 percent / imidazole / dimethylformamide / 1 h / Ambient temperature
11: 65.4 percent / 5percent KOH / methanol / 4 h / Heating
12: 90 percent / chromium oxide, pyridine / 14 h / Ambient temperature
13: 134 mg / tetrahydrofuran / 1 h / -78 °C
14: 60 mg / sodium acetate, m-chloroperbenzoic acid / CHCl3 / 1 h / 0 °C
15: 88 percent / chromium oxide, pyridine / 5 h / Ambient temperature
16: 1.) H2, 2.) NaOH / 1.) platinum oxide / 1.) ethyl acetate, 1 atm, 1.5 h, 2.) THF, RT, 1 h
17: 40 percent / tetrahydrofuran; diethyl ether / 2 h / -78 °C
18: acetic acid / methanol; H2O; tetrahydrofuran / 10 h / 50 °C
With
pyridine; 1H-imidazole; chromium(III) oxide; potassium hydroxide; sodium hydroxide; selenium(IV) oxide; borane; hydrogen bromide; hydrogen; dihydrogen peroxide; bromine; sodium acetate; pyridinium p-toluenesulfonate; lithium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; lithium bromide;
platinum(IV) oxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; chloroform; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jo00365a014