Multi-step reaction with 8 steps
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: diethylzinc / toluene; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 0.5 h / -78 - 0 °C / Inert atmosphere
2.3: 0.33 h / -78 - -20 °C / Inert atmosphere
3.1: cerium(III) chloride; lithium chloride / diethyl ether; tetrahydrofuran / 3 h / -78 °C / Inert atmosphere
3.2: 2.5 h / -78 - 0 °C / Inert atmosphere
4.1: pyridinium p-toluenesulfonate / benzene / 3.17 h / 20 °C / Inert atmosphere
5.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / -78 - -5 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 4 h / -78 °C / Inert atmosphere
7.2: 0.67 h / -78 - 0 °C / Inert atmosphere
8.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.03 h / 0 °C / Inert atmosphere
8.2: 1 h / 0 - 20 °C / Inert atmosphere
With
cerium(III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; diethylzinc; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; dichloromethane; toluene; benzene;
DOI:10.1021/ja307207q