Multi-step reaction with 11 steps
1: 1.) NCS, 2.) EtN(i-Pr)2 / 1.) DMF, r.t., 20 min, 2.) 16 h
2: K2CO3 / methanol / 1 h / Heating
3: NaOH / methanol / Ambient temperature
4: Et3N / tetrahydrofuran / 3 h / Ambient temperature
5: Et3N, DMAP / CH2Cl2 / Ambient temperature
6: 1.) NCS, 2.) EtN(i-Pr)2 / 1.) DMF, r.t., 2 h, 2.) 16 h
7: 90 percent / K2CO3 / methanol / 4 h / Ambient temperature
8: 96 percent / NaOH / methanol / Ambient temperature
9: Et3N / tetrahydrofuran / 3 h / Ambient temperature
10: Et3N, DMAP / CH2Cl2 / Ambient temperature
11: 1.) NCS, 2.) EtN(i-Pr)2 / 1.) DMF, r.t., 6 h, 2.) 16 h
With
dmap; sodium hydroxide; N-chloro-succinimide; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo00073a040