Multi-step reaction with 7 steps
1: aq. NaHCO3, KI3 / 1,2-dichloro-ethane / 0.5 h / Heating
2: 1.) 57percent aq. HI, Ac2O, 50percent aq. H3PO2 / 1.) 0 deg C, 5 min, 2.) 0 deg C, 20 min
3: (COCl)2, DMF / CH2Cl2 / 0.5 h / Ambient temperature
4: DMAP / CH2Cl2 / 0.33 h / Ambient temperature
5: 98 percent / H2 / 10percent Pd/C / tetrahydrofuran / 2.5 h / Ambient temperature
6: aq. NaHCO3, KI3 / CH2Cl2 / 0.03 h
7: 1.) SnCl2, 2.) AgOAc, aq. p-TsOH / 1.) CH2Cl2, 0 deg C, 30 min, 2.) THF, 13 h
With
dmap; oxalyl dichloride; potassium triiodide; hydrogen iodide; hydrogen; silver(I) acetate; hypophosphorous acid; acetic anhydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; N,N-dimethyl-formamide; tin(ll) chloride;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1039/p19960002079