Multi-step reaction with 8 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere
2.1: methanol / 65 °C / Inert atmosphere
3.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere
3.2: 2 h / 75 °C / Inert atmosphere
3.3: 20 °C / Inert atmosphere
4.1: triethylamine / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
5.1: sodium tetrahydroborate / ethanol / 1.5 h / Inert atmosphere
6.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere
7.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 1.5 h / Inert atmosphere
8.1: N,N-dimethyl acetamide / 3 h / 40 °C / Inert atmosphere
8.2: 0.67 h / -40 °C / Inert atmosphere
With
methanol; sodium tetrahydroborate; sodium tris(acetoxy)borohydride; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; 1,2-dichloro-ethane; N,N-dimethyl-formamide;