Multi-step reaction with 10 steps
1.1: sodium hydroxide; ethanol; water / 6 h / 60 - 100 °C
2.1: sodium carbonate / water / 1 h / 100 °C
3.1: potassium carbonate / N,N-dimethyl-formamide / 14 h / 20 °C
4.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 18 h / 20 °C
5.1: selenium(IV) oxide / 1,4-dioxane / 12 h / Heating / reflux
6.1: methyllithium / tetrahydrofuran; diethyl ether / 1 h / -78 °C
6.2: 5 h / -78 - -30 °C
7.1: 4-methylmorpholine N-oxide / dichloromethane / 2 h / 20 °C / Molecular sieve
7.2: 14 h / 20 °C
8.1: titanium(IV) isopropylate / tetrahydrofuran / 14 h / 20 °C
8.2: 2 h / 20 °C
9.1: triethylamine / dichloromethane / 4 h / 20 °C
10.1: N-Bromosuccinimide / dichloromethane / 4 h / 20 °C
With
titanium(IV) isopropylate; selenium(IV) oxide; sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); ethanol; water; methyllithium; sodium carbonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; 1,4-dioxane; tetrachloromethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;