Multi-step reaction with 8 steps
1: 94.7 percent / 4-dimethylaminopyridine / pyridine / 3.5 h / 0 deg C then rt., 3.5 h
2: 48 percent / iodosobenzene diacetate, iodine / CCl4 / 2 h / Heating; Irradiation
3: 89 percent / silver carbonate / acetone; H2O / 1.) 2.5 h 2.) reflux, overnight
4: 85 percent / PCC / CH2Cl2 / 1.5 h
5: 50 percent / tetrahydrofuran / 1 h / -20 - 0 °C
6: 3.0 g / NaOH / tetrahydrofuran; methanol; H2O / 6.5 h / Heating
7: 91 percent / pyridine / dioxane / cooling then rt., 30 min
8: 1.) Me3SiOTf, molecular sieves 4 Angstroem / 1.) C2H4Cl2, -20 deg C, 1 h 2.) C2H4Cl2, -20 deg C, 14 h
With
pyridine; dmap; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; iodine; silver carbonate; pyridinium chlorochromate;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; tetrachloromethane; dichloromethane; water; acetone;
DOI:10.1016/S0040-4020(01)89488-6