Multi-step reaction with 8 steps
1: 1.) sodium hydride / 1.) DMF, 20 deg C, 1 h; 2.) DMF, 20 deg C, 0.5 h
2: 1.) potassium tert-butoxide; 2.) mercury(II) oxide, mercury(II) chloride / 1.) methyl sulfoxide, 100 deg C, 1 h; 2.) acetone, water
3: 98.5 percent / methyl sulfoxide, oxalyl chloride / CH2Cl2 / 0.25 h / -60 °C
4: 1.) butyl-lithium / 1.) hexane, benzene, 15 min; 2.) hexane, benzene, reflux, 10 min
5: m-chloroperoxybenzoic acid / CHCl3 / 1 h / Heating
6: lithium aluminum hydride / tetrahydrofuran / 0.17 h
7: 82 percent / pyridine / CH2Cl2 / Ambient temperature
8: 58.5 percent / molecular sieves 4 Angstroem / nitromethane / 20 h / Heating
With
pyridine; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; potassium tert-butylate; sodium hydride; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; mercury dichloride; mercury(II) oxide;
In
tetrahydrofuran; nitromethane; dichloromethane; chloroform;
DOI:10.1016/0008-6215(85)85189-2