Multi-step reaction with 14 steps
1.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C
1.2: 24 h / 20 °C
2.1: Jones reagent / acetone / 0 °C
3.1: ammonium chloride / water; ethanol / 15 h / 20 °C
3.2: 48 h / 100 °C
4.1: sodium hydroxide / 19 h / 100 °C / Sealed tube
4.2: 18 h / 20 °C
5.1: diethyl ether / 0.5 h / 0 °C
6.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C
7.1: 1H-imidazole / N,N-dimethyl-formamide / 0.25 h / 0 °C
7.2: 0 - 20 °C
8.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C
9.1: acetic acid / methanol / 0 - 20 °C
9.2: 16 h / 0 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C
11.1: dmap; triethylamine / dichloromethane / 0 - 20 °C
12.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
13.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C
14.1: sodium hydride / tetrahydrofuran / 0 - 20 °C
With
1H-imidazole; dmap; Jones reagent; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; ammonium chloride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;