Multi-step reaction with 13 steps
1.1: sodium hydride / dimethyl sulfoxide / 0.5 h / 0 °C
1.2: 0 - 20 °C
2.1: aluminum (III) chloride / dichloromethane / 0.17 h / 25 °C
2.2: 25 °C
3.1: sodium tetrahydroborate; trifluoroacetic acid / dichloromethane / 0 - 25 °C / Inert atmosphere
4.1: caesium carbonate / tetrahydrofuran; methanol / 2 h / 70 °C
5.1: ozone / N,N-dimethyl-formamide / 0.13 h / -5 °C
6.1: hydrogenchloride / acetone / 24 h
7.1: hydrogenchloride / water / 24 h
8.1: potassium acetate / ethanol / 5 h / Reflux
9.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium(0) / 15 h / 14 °C
10.1: hydrogen / nickel / tetrahydrofuran / 25 °C / 760.05 Torr
11.1: potassium acetate / toluene
12.1: isopentyl nitrite / toluene / 18 h / 80 °C
13.1: methanol; potassium carbonate
With
hydrogenchloride; methanol; aluminum (III) chloride; sodium tetrahydroborate; hydrogen; potassium acetate; sodium hydride; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; ozone; trifluoroacetic acid; isopentyl nitrite;
tris-(dibenzylideneacetone)dipalladium(0); nickel;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;