Multi-step reaction with 9 steps
1: lithium aluminium tetrahydride / tetrahydrofuran; 2-methyltetrahydrofuran / 60 °C / Large scale reaction
2: thionyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / -17 - -3 °C / Large scale reaction
3: sodium periodate; rhodium(III) chloride hydrate / acetonitrile / 20 °C / Large scale reaction
4: potassium 2-methylbutan-2-olate / N,N-dimethyl acetamide; toluene / 24.5 h / 20 - 25 °C / Large scale reaction
5: toluene-4-sulfonic acid; acetic acid / Isopropyl acetate / 3.5 h / 20 - 60 °C / Large scale reaction
6: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran / 0.5 h / 50 °C / Large scale reaction
7: potassium carbonate / tetrahydrofuran; toluene / 3 h / 20 °C
8: sodium hydroxide / 6 h / 20 °C / Large scale reaction
9: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 35 °C / Large scale reaction
With
sodium periodate; lithium aluminium tetrahydride; formic acid; thionyl chloride; rhodium(III) chloride hydrate; palladium 10% on activated carbon; potassium 2-methylbutan-2-olate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide;
In
tetrahydrofuran; 2-methyltetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; Isopropyl acetate; toluene; acetonitrile;
DOI:10.1021/jo300046v