Multi-step reaction with 11 steps
1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane
2.1: diisobutylaluminium hydride; hydrogen bromide / dichloromethane / Cooling with ice
3.1: toluene-4-sulfonic acid / methanol / 1 h / 50 °C
4.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 - 0 °C / Cooling with ice
4.2: 0.67 h / -78 - 0 °C / Cooling with ice
5.1: hydrogenchloride / hexane; tetrahydrofuran; water / 3 h / Cooling with ice
6.1: n-butyllithium; diphenyl diselenide / hexane; tetrahydrofuran / 8 h / -60 - -20 °C
7.1: dmap; pyridine / dichloromethane / 3 h / 0 °C / Cooling with ice
8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 7 h / 0 °C / Cooling with ice
9.1: caesium carbonate / tetrahydrofuran / 1.33 h / 0 - 20 °C / Cooling with ice
10.1: diisobutylaluminium hydride / toluene / 2.33 h / -78 - 0 °C / Cooling with ice
11.1: sodium amalgam; disodium hydrogenphosphate / methanol / 2.5 h / 0 °C / Cooling with ice
With
pyridine; hydrogenchloride; dmap; disodium hydrogenphosphate; N-Bromosuccinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); diphenyl diselenide; sodium amalgam; hydrogen bromide; diisobutylaluminium hydride; caesium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; toluene;
DOI:10.1039/c3ob40115d