Multi-step reaction with 7 steps
1: 1.) O3, 2.) dimethyl sulfide / 1.) CH2Cl2, MeOH, -78 deg C, 0.5 h, 2.) r.t., 3 h
2: 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
3: Et3N, methanesulfonyl chloride / CH2Cl2 / 1 h
4: aq. K2CO3 / methanol / 3.5 h / Ambient temperature
5: diethyl ether
6: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 0.5 h, 2.) -78 deg C to r.t.
7: 92 percent / aq. K2CO3 / methanol / Ambient temperature
With
n-butyllithium; oxalyl dichloride; dimethylsulfide; potassium carbonate; ozone; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1039/a701589e