Multi-step reaction with 14 steps
1.1: ethanol / 6 h / 760.05 Torr / Reflux
2.1: hydrogen bromide; acetic acid / 2 h / 40 - 55 °C / 760.05 Torr
2.2: 760.05 Torr / Cooling with ice
3.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux
3.2: 760.05 Torr / pH 1
4.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr
5.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr
6.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere
7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr
7.2: 2 h / 760.05 Torr
8.1: osmium(VIII) oxide / water; 1,4-dioxane / 0.5 h / 20 °C / 760.05 Torr
8.2: 16 h / 20 °C / 760.05 Torr
9.1: caesium carbonate / ethanol; ethyl acetate / 2 h / 50 °C / 760.05 Torr
10.1: sodium tetrahydroborate; methanol / 16 h / 20 °C / 760.05 Torr
10.2: 760.05 Torr
11.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 16 h / 20 °C / 760.05 Torr / Molecular sieve
12.1: tetrahydrofuran / -78 °C / 760.05 Torr / Inert atmosphere
12.2: 760.05 Torr
13.1: triphenylphosphine / tetrahydrofuran / 0.08 h / 0 °C / 760.05 Torr / Inert atmosphere
13.2: 2.33 h / 0 - 20 °C / 760.05 Torr / Inert atmosphere
14.1: palladium 10% on activated carbon; hydrogen / methanol / 0.5 h / 20 °C / 760.05 Torr
With
methanol; sodium tetrahydroborate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium(0); tetrapropylammonium perruthennate; oxalyl dichloride; palladium 10% on activated carbon; water; hydrogen bromide; hydrogen; sodium hydride; caesium carbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N,N-dimethyl-formamide; triphenylphosphine; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;