Multi-step reaction with 10 steps
1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.53 h / -78 - 20 °C / Inert atmosphere
1.2: 2 h / 20 °C
2.1: 3,3-Dimethylbut-1-yne; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / 1,2-dimethoxyethane; ethanol / 16 h / 80 °C / Inert atmosphere; Sealed tube
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / -78 - 20 °C
4.1: N-Bromosuccinimide / dichloromethane; tetrahydrofuran / 1 h / 0 - 20 °C
5.1: Dess-Martin periodane / dichloromethane / 1.5 h / -78 - 20 °C
6.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
6.2: 0.17 h / 20 °C
7.1: pyridinium chlorochromate / dichloromethane; tetrahydrofuran / 62 h / 20 °C
8.1: nickel dichloride; sodium tetrahydroborate; methanol / water; tetrahydrofuran; ethyl acetate; chlorobenzene / 0.67 h / -30 - 20 °C
9.1: cesium fluoride; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II) / water; 1,4-dioxane / 16 h / 90 °C / Inert atmosphere
10.1: lithium hydroxide monohydrate / water; tetrahydrofuran; ethanol / 2 h / 50 °C
With
methanol; sodium tetrahydroborate; potassium phosphate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; lithium hydroxide monohydrate; 3,3-Dimethylbut-1-yne; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium tert-butylate; Dess-Martin periodane; diisopropylamine; cesium fluoride; pyridinium chlorochromate; nickel dichloride;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; chlorobenzene;
2.1: |Suzuki Coupling / 6.1: |Wittig Olefination / 6.2: |Wittig Olefination;