Multi-step reaction with 9 steps
1: 48 percent / NaH / benzene / 3 h / Heating
2: 64 percent / NaH / dimethylformamide / 1.) 60 deg C, 0.5 h, 2.) 16 h
3: 95 percent / aq. K2CO3 / methanol / 6 h / 50 °C
4: 1.) O3, 2.) dimethyl sulfide / 1.) CH2Cl2, MeOH, -78 deg C, 0.5 h, 2.) r.t., 3 h
5: 66 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 10 min, 2.) -78 deg C, 2.5 h; -78 deg C to r.t., 1 h
6: 90 percent / Et3N, methanesulfonyl chloride / CH2Cl2 / 1 h
7: aq. K2CO3 / methanol / 3.5 h / Ambient temperature
8: diethyl ether
9: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) -78 deg C to r.t.
With
n-butyllithium; oxalyl dichloride; dimethylsulfide; sodium hydride; potassium carbonate; ozone; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1039/a701589e