Multi-step reaction with 12 steps
1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 20 °C
2.1: triethylamine / 1,2-dichloro-ethane / 20 °C
3.1: Dess-Martin periodane / dichloromethane / 3.7 h / 0 - 20 °C / Inert atmosphere
4.1: hydroxylamine hydrochloride; sodium acetate / ethanol / 20 - 80 °C
5.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.87 h / 20 °C
6.1: triethylamine / dichloromethane / 1.5 h / 0 - 20 °C
7.1: trifluoroacetic acid / 1 h / 20 °C
8.1: sodium periodate / water; tetrahydrofuran / 1 h / 20 °C
9.1: sodium tetrahydroborate; methanol / 0.5 h / 20 °C
10.1: trifluoroacetic acid / 1,2-dichloro-ethane / 1 h / 20 - 80 °C
11.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
12.1: methanol / titanium(IV)isopropoxide; acetic acid / 1,2-dichloro-ethane / 1.33 h / 20 °C
12.2: 20 °C
With
methanol; sodium tetrahydroborate; sodium periodate; N-chloro-succinimide; hydroxylamine hydrochloride; sodium acetate; Dess-Martin periodane; triethylamine; trifluoroacetic acid;
titanium(IV)isopropoxide; acetic acid;
In
tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;