Multi-step reaction with 8 steps
1: 91 percent / LiAlH4 / diethyl ether / Ambient temperature
2: 64 percent / NEt3, DMAP / dimethylformamide / Ambient temperature
3: 98 percent / oxalyl chloride, DMSO, NEt3 / CH2Cl2 / 1) -70 deg C, 15 min, 2) -70 deg C to RT
4: 1) oxalyl chloride, DMSO, NEt3, 2) p-TsOH / 1) CH2Cl2, a) -70 deg C, 15 min, b) -70 deg C to RT, 2) benzene, 2h, reflux
5: 98 percent / 2N HCl / acetone / Ambient temperature
6: 86 percent / LiAlH4 / diethyl ether / Ambient temperature
7: 64 percent / NEt3, DMAP / dimethylformamide / Ambient temperature
8: 99 percent / imidazole, DMAP / dimethylformamide / Ambient temperature
With
1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine;
In
diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)86756-9