Multi-step reaction with 10 steps
1.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere
2.1: water; lithium hydroxide / methanol; tetrahydrofuran / 10 h
3.1: triethylamine / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere
4.1: lithium chloride / tetrahydrofuran / 5 h / -20 - 0 °C / Inert atmosphere
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 3 h / -78 °C / Inert atmosphere
6.1: lithium borohydride / methanol; tetrahydrofuran; diethyl ether / 1 h / -10 °C / Inert atmosphere
7.1: pyridine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
8.1: Dowex 50WX8 / methanol / 48 h / 20 °C / Inert atmosphere
9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.67 h / 0 - 20 °C / Inert atmosphere
9.2: 0.5 h / 0 - 20 °C / Inert atmosphere
10.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere
10.2: 0.67 h / -78 °C / Inert atmosphere
With
pyridine; dmap; sodium tetrahydroborate; lithium borohydride; n-butyllithium; nickel(II) chloride hexahydrate; water; sodium hexamethyldisilazane; sodium hydride; triethylamine; lithium chloride; lithium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; mineral oil;
DOI:10.1002/hlca.201200519