Multi-step reaction with 8 steps
1: 1.) NaOMe / 1.) MeOH, 20 min, 2.) MeOH, reflux, 1 h
2: 90.2 percent / NaBH4 / propan-2-ol / 8 h / Heating
3: SOCl2 / 1,2-dichloro-ethane / 1 h / Heating
4: AlCl3 / 1,2-dichloro-ethane / 0.25 h / Heating
5: 1.) (TMS)2NLi / 1.) THF, -60 deg C, 10 min, 2.) THF, -70 deg C, 20 min
6: 92.4 percent / m-chloroperbenzoic acid / CH2Cl2 / 0.5 h / Ambient temperature
7: N-bromosuccinimide, dibenzoyl peroxide / 1,2-dichloro-ethane / 2 h / Heating
8: 86 percent / K2CO3 / acetonitrile / 4 h / Heating
With
sodium tetrahydroborate; N-Bromosuccinimide; aluminium trichloride; thionyl chloride; sodium methylate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; dibenzoyl peroxide;
In
dichloromethane; 1,2-dichloro-ethane; isopropyl alcohol; acetonitrile;
DOI:10.1021/jm00014a024