Multi-step reaction with 16 steps
1.1: potassium carbonate / acetonitrile / 60 °C
2.1: hydrogen / Raney nickel / methanol / 2 h / 20 °C
3.1: hydrogenchloride; sodium nitrite / water / 2 h / 0 °C
3.2: 1 h / 80 °C
4.1: triethylamine / tetrakis(triphenylphosphine) palladium(0) / acetonitrile / 15 h / 65 °C / 2585.81 Torr
5.1: sodium tetrahydroborate / methanol / 12 h / 20 - 40 °C
6.1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 12 h / 0 - 20 °C
7.1: n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran / 3 h / -78 °C
7.2: 20 h / -78 - 20 °C
8.1: lithium hydroxide; water; dihydrogen peroxide / tetrahydrofuran / 12 h / 0 - 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 24 h / -78 - 20 °C
9.2: 0 °C
10.1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 12 h / 0 - 20 °C
11.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C
11.2: 13 h / -78 - 20 °C
12.1: hydrogenchloride; water / acetonitrile / 5 h / 20 °C
12.2: 0 °C
13.1: triethylamine / dichloromethane / 20 h / 0 - 20 °C
14.1: sodium tetrahydroborate / ethanol / 12 h / 20 - 40 °C
15.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.75 h / -60 - -50 °C
16.1: magnesium / tetrahydrofuran / 0.5 h / Heating / reflux
16.2: -78 - 20 °C
With
hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; water; hydrogen; dihydrogen peroxide; potassium carbonate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium nitrite;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetonitrile;
15.1: Swern Oxidation;