Multi-step reaction with 11 steps
1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2.75 h / -78 °C
1.2: 3 h / -78 °C
2.1: hydrogenchloride; water; acetic acid / 1 h / 20 °C
3.1: sodium hydride / tetrahydrofuran / 18 h / 0 - 60 °C
3.2: 1 h / 0 °C
4.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C
4.2: 0.17 h / 0 °C
4.3: 0.25 h / 0 °C
5.1: carbonochloridic acid 1-chloro-ethyl ester / tetrahydrofuran / 0.25 h / 0 °C
5.2: 16 h / 65 °C
5.3: 0.17 h / 20 °C
6.1: tetrahydrofuran / 0.08 h / 20 °C
7.1: sodium hydroxide; water; isopropyl alcohol / tetrahydrofuran / 18 h / 0 - 20 °C
8.1: 15-crown-5; sodium hydride / tetrahydrofuran / 1 h / 0 °C
9.1: hydrogen / palladium 10% on activated carbon / ethanol / 1 h
10.1: dimethylsulfide borane complex / tetrahydrofuran; toluene / 24 h / 20 °C
11.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 60 h / 0 - 20 °C
With
hydrogenchloride; sodium hydroxide; n-butyllithium; 15-crown-5; carbonochloridic acid 1-chloro-ethyl ester; dimethylsulfide borane complex; water; hydrogen; sodium hydride; acetic acid; methanesulfonyl chloride; diisopropylamine; N-ethyl-N,N-diisopropylamine; isopropyl alcohol;
palladium 10% on activated carbon;
In
tetrahydrofuran; ethanol; hexane; toluene;