Multi-step reaction with 10 steps
1.1: chloro-trimethyl-silane; lithium hexamethyldisilazane / tetrahydrofuran; diethyl ether / 2.83 h / -78 - -20 °C / Inert atmosphere
2.1: di-tert-butyl dicarbonate; pyridine / ethyl acetate / 3 h / 20 °C / Inert atmosphere
2.2: 2 h / Inert atmosphere
3.1: aluminum (III) chloride; lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 12 h / 0 °C / Inert atmosphere
4.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere
5.1: hydrogenchloride / methanol / 9.17 h / 0 - 20 °C / Inert atmosphere
6.1: dichloro bis(acetonitrile) palladium(II) / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
7.1: iodine / dichloromethane / 0 - 20 °C / Inert atmosphere
7.2: 0.5 h / -78 - 0 °C / Inert atmosphere
8.1: chloro-trimethyl-silane; zinc / ethanol; ethylene dibromide / 0.08 h / 75 °C / Inert atmosphere
8.2: 2 h / 75 °C / Inert atmosphere
9.1: Jones reagent / acetone / 0 - 20 °C / Inert atmosphere
10.1: sodium hydroxide / water; diethyl ether / 17.5 h / 100 °C / Inert atmosphere
With
pyridine; hydrogenchloride; aluminum (III) chloride; dichloro bis(acetonitrile) palladium(II); lithium aluminium tetrahydride; chloro-trimethyl-silane; di-tert-butyl dicarbonate; Jones reagent; iodine; triethylamine; sodium hydroxide; lithium hexamethyldisilazane; zinc;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; ethylene dibromide; acetone;
9.1: |Jones Oxidation;
DOI:10.1002/ejoc.201402452