Multi-step reaction with 13 steps
1.1: diisobutylaluminium hydride / toluene / -78 °C
1.2: -78 - 20 °C
2.1: diethyl ether / 3 h / 0 - 20 °C
2.2: 0 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C
3.2: 1 h / -78 - 20 °C
4.1: tetra-N-butylammonium tribromide / methanol; dichloromethane / 24 h
5.1: hexamethylenetetramine / dichloromethane / 48 h / 20 °C
5.2: 2 h / Reflux
6.1: triethylamine / benzene / 6 h / Reflux
7.1: acetic acid / 5 h / Reflux
8.1: dihydrogen peroxide; acetic acid / dichloromethane / 0 - 20 °C
8.2: pH 9
9.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C
9.2: 3 h / -78 °C
10.1: sodium tetrahydroborate / ethanol / 3 h
11.1: thionyl chloride / acetonitrile / 3 h / 0 °C
12.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C
12.2: 20 °C
13.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C
With
sodium tetrahydroborate; n-butyllithium; thionyl chloride; oxalyl dichloride; hexamethylenetetramine; dihydrogen peroxide; tetra-N-butylammonium tribromide; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; mineral oil; benzene;