Multi-step reaction with 6 steps
1: 92 percent / K2CO3 / butan-2-one / 25 h / Heating
2: 1.) DMSO, oxalyl chloride / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, -78 deg C, 20 min
3: 1.) Mg / 1.) THF, reflux, 2 h, 2.) THF, RT, 1 h
4: 25 percent / ZnI, sodium cyanoborohydride / 1,2-dichloro-ethane / 18 h / Heating
5: 89 percent / H2 / 10percent Pd/C / ethanol; ethyl acetate / 1.5 h / 2068.6 Torr
6: 98 percent / m-chloroperbenzoic acid / CH2Cl2 / 1.) 5 deg C, 30 min, 2.) RT, 30 min
With
oxalyl dichloride; hydrogen; sodium cyanoborohydride; potassium carbonate; magnesium; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide;
palladium on activated charcoal;
In
ethanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; butanone;
DOI:10.1021/jm00085a019