Multi-step reaction with 9 steps
1: 1.) (COCl)2, DMSO; 2.) Et3N / CH2Cl2 / -63 °C
2: 77 percent / nBuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
3: acetone / Heating
4: 87 percent / SO2Cl2, Ph3P, 3 Angstroem molecular sieves / CH2Cl2 / 3 h / Ambient temperature
5: 75 percent / 4-dimethylaminopyridine (DMAP) / CH2Cl2 / 3 h / Ambient temperature
6: 3M HCl/MeOH / 3 h / Ambient temperature
7: 44 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU), 4-dimethylaminopyridine (DMAP) / CH2Cl2 / 4 h / Ambient temperature
8: HCl/MeOH / 3 h / Ambient temperature; 0 to 25 deg C
9: 32 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU), 4-dimethylaminopyridine (DMAP) / CH2Cl2 / Ambient temperature
With
hydrogenchloride; methanol; dmap; n-butyllithium; sulfuryl dichloride; oxalyl dichloride; 3 A molecular sieve; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine;
In
tetrahydrofuran; hexane; dichloromethane; acetone;