Multi-step reaction with 18 steps
1: 1.) dimethylsulphoxide, oxalyl chloride; 2.) triethylamine / 1.) THF, -80 deg C --> -40 deg C, 5 min; 2.) 0 deg C, 5 min
2: tetrahydrofuran / 2 h / -80 °C
3: 80 percent / pyridine / 0 °C
4: 88 percent / imidazole / dimethylformamide / Ambient temperature
5: 80 percent / dimethylformamide / 12 h / 70 °C
6: di-isobutylaluminium hydride / CH2Cl2 / 5 h / Ambient temperature; 1.) -78 deg C --> room temp., 1 h
7: CH2Cl2 / 0 deg C, then room temp. overnight
8: 60 percent / di-isobutylaluminium hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / -78 deg C --> room temp., overnight
9: triethylamine, dimethylaminopyridine / CH2Cl2 / 0 °C
10: sodium iodide / tetrahydrofuran / 12 h
11: 80 percent / tetrahydrofuran / -20 °C
12: lithium aluminium hydride / diethyl ether / 1 h / 0 °C
13: pyridine / 0 °C
14: 90 percent / sodium / methanol / Ambient temperature
15: 90 percent / KHSO5 / H2O; ethanol / 5 h / 0 °C
16: 1.) t-butyl-lithium / 1.) hexane, THF, -80 deg C; -50 deg C, 1 h; 2.) THF, -50 deg C, 1 h
17: tetrahydrofuran / 0.17 h / -50 °C / 2.) room temp., 2 h
18: sodium amalgam, sodium dihydrogen orthophosphate / methanol; tetrahydrofuran / 5 h / -20 °C
With
1H-imidazole; dmap; sodium dihydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; potassium peroxomonosulfate; oxalyl dichloride; diisobutylaluminum hydride; tert.-butyl lithium; sodium; dimethyl sulfoxide; triethylamine; sodium iodide;
In
tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;