Multi-step reaction with 10 steps
1: 81 percent / 1N aq. HCl / tetrahydrofuran / 12 h / Heating
2: 82 percent / Et3N / ethanol; CH2Cl2 / 0.5 h / Ambient temperature
3: 88 percent / DDQ / 1,2-dichloro-ethane / 80 °C
4: ethanethiol, AlCl3 / CH2Cl2 / 5 h / Ambient temperature
5: Et3N / CH2Cl2 / 5 h / Ambient temperature
6: 60 percent / DIBAL-H / toluene / -100 - -70 °C
7: 99 percent / MgSO4 / CH2Cl2 / 4 h / Ambient temperature
8: toluene; tetrahydrofuran / 1.5 h / Ambient temperature
9: 87 percent / K2CO3 / methanol / 0.25 h
10: PPh3, DEAD / toluene / 2 h / Ambient temperature
With
hydrogenchloride; aluminium trichloride; diisobutylaluminium hydride; magnesium sulfate; potassium carbonate; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ethanethiol; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; toluene;
DOI:10.1021/jm970688z