Multi-step reaction with 12 steps
1.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C
1.2: 1 h / -78 - 20 °C
2.1: diethyl ether / 3 h / 0 - 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
3.2: 1 h / -78 - 20 °C
4.1: tetra-n-butylammonium tribromide / dichloromethane; methanol / 24 h
5.1: hexamethylenetetramine / dichloromethane / 48 h / 20 °C
5.2: 2 h / Reflux
6.1: triethylamine / benzene / 6 h / Reflux
7.1: dihydrogen peroxide; acetic acid / dichloromethane / 6.67 h / 0 - 20 °C
8.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C
8.2: 3 h / -78 °C
9.1: sodium tetrahydroborate / ethanol / 3 h
10.1: thionyl chloride / acetonitrile / 3 h / 0 °C
11.1: potassium carbonate; 18-crown-6 ether / acetonitrile / 8 h / 60 °C
12.1: sodium hydroxide / methanol / 3 h / 65 °C
12.2: pH 3
With
sodium tetrahydroborate; n-butyllithium; thionyl chloride; tetra-n-butylammonium tribromide; oxalyl dichloride; 18-crown-6 ether; hexamethylenetetramine; dihydrogen peroxide; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; sodium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; benzene;