Multi-step reaction with 10 steps
1.1: hexane; diethyl ether / 1.25 h / -70 - -60 °C / Inert atmosphere
1.2: 4 h / -60 - 10 °C
2.1: sodium hydrogencarbonate; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water; tert-butyl alcohol / 20 °C
3.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
3.2: 6.33 h / 20 °C / Inert atmosphere; Reflux
4.1: hydrogenchloride / ethanol / 0.33 h / 70 °C
5.1: toluene-4-sulfonic acid / ethanol / 0.75 h / 45 °C
6.1: n-butyllithium / diethyl ether / 0.75 h / -78 °C / Inert atmosphere
6.2: -78 - 20 °C
7.1: 1,1'-carbonyldiimidazole / 1-methyl-pyrrolidin-2-one / 2 h / 20 °C / Inert atmosphere
7.2: 2 h / 20 °C
8.1: titanium(IV) tetraethanolate / tetrahydrofuran / 72 h
9.1: n-butyllithium / hexane; tetrahydrofuran / 1.42 h / -72 - -70 °C / Inert atmosphere
9.2: 1.25 h / -70 °C
10.1: hydrogenchloride / diethyl ether; methanol / 2.5 h / 20 °C
With
hydrogenchloride; titanium(IV) tetraethanolate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; potassium tert-butylate; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1,1'-carbonyldiimidazole;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; ethanol; hexane; water; tert-butyl alcohol;