Multi-step reaction with 7 steps
1: 76 percent / N,N-dimethylaniline, Et3N / CH2Cl2 / 1) 0 deg C, 15 min, 2) r.t., 30 min
2: 85 percent / Rh2<-CH2-CH2-CH(CO2Me)-N=CO->4 / CH2Cl2 / Heating
3: 1) Me3Al / 1) hexane, ClCH2CH2Cl, r.t., 1 h, 2) ClCH2CH2Cl, 83 deg C, 4 h
4: 87 percent / pyridinium chlorochromate / CH2Cl2 / 12 h / Ambient temperature
5: K2CO3 / methanol / 12 h / Ambient temperature
6: 85 percent / 8 N Jones reagent / acetone / 2 h / 0 - 5 °C
7: 74 percent / 1-hydroxybenzotriazole, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 24 h / Ambient temperature
With
jones reagent; trimethylaluminum; potassium carbonate; benzotriazol-1-ol; N,N-dimethyl-aniline; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; pyridinium chlorochromate;
Rh2<-CH2-CH2-CH(CO2Me)-N=CO->4;
In
methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)90212-1