Multi-step reaction with 8 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -78 °C / Inert atmosphere
1.2: 1.5 h / 20 °C / Inert atmosphere
2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 - 20 °C / Inert atmosphere
2.2: 2.08 h / -78 - 20 °C / Inert atmosphere
3.1: hydrogenchloride / methanol; water / 16 h / 20 °C
4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 20 - 80 °C / Inert atmosphere
5.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 16 h / 20 °C / Inert atmosphere
6.1: ammonium cerium (IV) nitrate / acetonitrile; water / 16 h / 20 °C
7.1: sodium hydrogencarbonate / ethanol / 16 h / 0 - 20 °C / Inert atmosphere
8.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 16 h / 0 - 20 °C
8.2: 0.5 h / 20 °C
With
hydrogenchloride; ammonium cerium (IV) nitrate; oxalyl dichloride; dihydrogen peroxide; potassium hexamethylsilazane; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; lithium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; toluene; acetonitrile;
1.1: |Swern Oxidation / 1.2: |Swern Oxidation;
DOI:10.1016/j.tetlet.2013.09.043