Multi-step reaction with 8 steps
1: 87 percent / pyridinium chlorochromate / CH2Cl2 / 2 h
2: 59 percent / zinc / benzene / 36 h / Heating
3: 97 percent / ammonia, lithium / tetrahydrofuran / 2 h / Heating
4: 81 percent / lithium aluminum hydride / tetrahydrofuran / 10 h / Heating
5: 87 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h
6: 1.) potassium tert-butoxide / 1.) THF, 0 deg C, 2.0 h, 2.) THF, RT, 5.0 h
7: 71 percent / Jones reagent / acetone / 2 h
8: 1.) n-butyllithium / 1.) ether, hexane, 0 deg C, 1.0 h, 2.) ether, hexane, RT, 5.0 h
With
lithium aluminium tetrahydride; n-butyllithium; jones reagent; potassium tert-butylate; ammonia; lithium; pyridinium chlorochromate; zinc;
In
tetrahydrofuran; dichloromethane; acetone; benzene;
DOI:10.1021/jo00374a022