Multi-step reaction with 12 steps
1: potassium hydroxide / ethanol; N,N-dimethyl-formamide / 1.25 h / -2 °C
2: palladium on carbon; formic acid; ammonium formate / methanol / 1 h
3: 2 h / 0 °C
4: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / Reflux
5: diphenyl phosphoryl azide; triphenylphosphine; diethylazodicarboxylate / toluene / 9 h
6: potassium tert-butylate / tetrahydrofuran / 6 h / 0 °C
7: 1,1,1,3',3',3'-hexafluoro-propanol; trimethylsilyl trifluoromethanesulfonate; bis-[(trifluoroacetoxy)iodo]benzene / water / 1 h / 0 °C
8: hydrogenchloride / methanol / 36 h / 20 °C
9: bis-[(trifluoroacetoxy)iodo]benzene / 2,2,2-trifluoroethanol / 7 h / 20 °C
10: boron trifluoride diethyl etherate / dichloromethane / 7 h / 0 - 20 °C
11: iodopentafluorobenzene bis(trifluoroacetate); sodium hydrogencarbonate / methanol; acetonitrile / 1.5 h / 20 °C / Molecular sieve
12: hydrogen bromide; p-methoxybenzylmercaptan; acetic acid / dichloromethane / 36 h / -78 - 4 °C
With
hydrogenchloride; lithium aluminium tetrahydride; formic acid; 1,1,1,3',3',3'-hexafluoro-propanol; trimethylsilyl trifluoromethanesulfonate; iodopentafluorobenzene bis(trifluoroacetate); diphenyl phosphoryl azide; palladium on carbon; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen bromide; ammonium formate; sodium hydrogencarbonate; p-methoxybenzylmercaptan; acetic acid; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; potassium hydroxide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; 2,2,2-trifluoroethanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;
5: Mitsunobu reaction / 12: Michael addition;
DOI:10.1039/c1ob05058c