Multi-step reaction with 12 steps
1.1: POCl3 / 0.5 h / 0 °C
1.2: 73 percent / 4 h / 80 °C
2.1: 53 percent / NaOEt / diethyl ether; ethanol / 3 h / -10 - 20 °C
3.1: 52 percent / toluene / 6 h / Heating
4.1: NaH / dimethylformamide / 0.25 h
4.2: dimethylformamide / 48 h / 20 °C
5.1: 37.5 g / aq. NaOH / methanol; tetrahydrofuran; dimethylformamide / 50 °C
6.1: 100 percent / LiAlH4 / tetrahydrofuran / 18 h / 20 °C
7.1: 26 percent / H2 / Pd/C / tetrahydrofuran; ethanol; CHCl3 / 18 h / 2327.17 - 2585.74 Torr
8.1: BBr3 / CHCl3 / 2.5 h / 20 °C
9.1: 0.43 g / Cs2CO3 / dimethylformamide / 18 h / 20 °C
10.1: CH2Cl2 / 1 h / 0 °C
11.1: 0.28 g / NH3 / CH2Cl2; dioxane / 0.5 h
12.1: 71 percent / aq. LiOH / methanol; tetrahydrofuran / 19 h / 20 °C
With
lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; ammonia; hydrogen; sodium ethanolate; boron tribromide; sodium hydride; caesium carbonate; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
1.2: Vilsmeier reaction;
DOI:10.1021/jm0401309