Multi-step reaction with 11 steps
1.1: CH2Cl2 / 1 h / 20 °C
2.1: NaH / ethanol / 2 h / Heating
3.1: tetrabutylammonium bromide; KOH / tetrahydrofuran; dimethylformamide / 0.17 h / 20 °C
3.2: 89 percent / tetrahydrofuran; dimethylformamide / 0.5 h / 20 °C
4.1: NaOH / ethanol / Heating
5.1: SOCl2 / 1 h / Heating
6.1: NH3 / CH2Cl2 / 0.67 h
7.1: 0.59 g / POCl3 / benzene / 7 h / Heating
8.1: p-toluenesulfonic acid monohydrate; trimethylstannylazide / xylene / 115 - 120 °C
9.1: aq. NaOH / CH2Cl2; tetrahydrofuran / 0.25 h / 20 °C
9.2: tetrahydrofuran; CH2Cl2 / 3 h / 20 °C
10.1: N-bromosuccinimide; dibenzoyl peroxide / CCl4 / Heating
11.1: NaH / dimethylformamide / 0.33 h / 0 °C
11.2: 0.18 g / dimethylformamide / 20 °C
With
potassium hydroxide; sodium hydroxide; N-Bromosuccinimide; thionyl chloride; tetrabutylammomium bromide; ammonia; sodium hydride; azidotrimethyltin; toluene-4-sulfonic acid; trichlorophosphate; dibenzoyl peroxide;
In
tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; xylene; benzene;
DOI:10.1021/jm031100t