Multi-step reaction with 12 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -76 °C
1.2: 2 h / -74 °C
2.1: potassium carbonate; methanol / 2 h / 20 °C
3.1: n-butyllithium / hexane; tetrahydrofuran / 0.92 h / -72 °C
3.2: 0.58 h / -72 °C
4.1: manganese(IV) oxide / dichloromethane / 15 h / 20 °C
5.1: triethylamine / ethanol / 0.5 h / 20 °C
5.2: 15 h / 20 °C
6.1: hydrogenchloride; water / tetrahydrofuran / 15 h / 20 °C
6.2: 0 °C
7.1: sodium tetrahydroborate; methanol / 2 h / 20 °C
8.1: dmap; pyridine / dichloromethane / 66 h / 20 °C
9.1: potassium carbonate; methanol / 4 h / 20 °C
10.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C
11.1: diethylamino-sulfur trifluoride / dichloromethane / 2 h / 20 °C
12.1: sodium hydroxide; water / tetrahydrofuran; methanol / 6 h / 20 °C
With
pyridine; hydrogenchloride; methanol; dmap; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; diethylamino-sulfur trifluoride; water; potassium carbonate; Dess-Martin periodane; triethylamine; sodium hydroxide;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane;