Multi-step reaction with 6 steps
2: 1.) CuBr / 1.) THF, ether, 0 deg C, 15 min, 2.) THF, -30 deg C, 4 h, then 0 deg C, 0.5 h
3: 78 percent / trimethyl orthoformate, p-TsOH / benzene / 6 h / Ambient temperature
4: 1.) O3, 2.) dimethyl sulfide / 1.) methanol, -78 deg C, 1 h, 2.) -78 deg C, 3 h, then rt, 4 h
5: 1.) LDA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, -78 deg C, 2 h, then rt, 8 h
6: 92 percent / aq. HCl / 3 h / Ambient temperature
With
hydrogenchloride; dimethylsulfide; toluene-4-sulfonic acid; ozone; copper(I) bromide; lithium diisopropyl amide; trimethyl orthoformate;
In
benzene;
DOI:10.1021/jo00033a023