Multi-step reaction with 8 steps
1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 30 min, 2.) -40 deg C, 5 min
2: triethylammonium chloride / CH2Cl2 / 48 h / Ambient temperature
3: Et3N, DMAP / 1.5 h / -5 °C
4: 180 - 200 °C
5: 1.) CuBr*Me2S / 1.) ether, -60 to -30 deg C, 20 min, 2.) -60 deg C, 15 min
6: 76 percent / t-BuOK / 1.) THF, 6 h, 2.) ether, overnight
7: H2 / Pd/C
8: TFA / 48 h
With
dmap; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; potassium tert-butylate; hydrogen; dimethyl sulfoxide; triethylamine;
palladium on activated charcoal; triethylamine hydrochloride; trifluoroacetic acid;
In
dichloromethane;
DOI:10.1021/jo00121a034