Multi-step reaction with 13 steps
1: p-TsOH*H2O / 2 h / Ambient temperature
2: n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 30 min, 2.) r.t., 70 min
3: p-TsOH*H2O / methanol / 1 h / Ambient temperature
4: 99 percent / pyridine / 3.5 h / Ambient temperature
5: 73 percent / dichloromaleic anhydride / 200 °C
6: 99 percent / 2 M KOH / ethanol / 19 h / Heating
7: 72 percent / CBr4, PPh3 / CH2Cl2 / 6 h / Ambient temperature
8: n-BuLi / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 3.5 h, 2.) -78 deg C to r.t., 17 h
9: p-TsOH*H2O / methanol / 1 h / Heating
10: 68 percent / CBr4, PPh3 / diethyl ether; CH2Cl2 / 1.) 0 deg C, 1 h, 2.) r.t., 17 h
11: 1.) EtMgBr, 2.) CuCN / 1.) THF, reflux, 1 h; r.t., 15 min, 2.) 0 deg C, 30 min; r.t., 15 h
12: H2, quinoline / 5percent Pd/BaSO4 / pyridine / 1.92 h / 750.06 Torr / Ambient temperature
13: 63 percent / AlI3, (+)-limonene / CS2 / 1.) r.t., 10 min, 2.) reflux, 30 min
With
pyridine; quinoline; potassium hydroxide; aluminium(III) iodide; n-butyllithium; dichloromaleic acid anhydride; carbon tetrabromide; ethylmagnesium bromide; hydrogen; (+)-limonene; toluene-4-sulfonic acid; triphenylphosphine;
Pd-BaSO4;
In
tetrahydrofuran; pyridine; methanol; carbon disulfide; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane;