Multi-step reaction with 13 steps
1: pyridine
2: K2CO3 / methanol
3: 1.) n-BuLi / 1.) THF, -20 deg C, 2 h, 2.) 17 h
4: 78 percent / NBS, AgNO3, 2,6-lutidine / H2O; acetonitrile / 0.12 h
5: LiAlH4, LiI / diethyl ether / 0.5 h / -100 °C
6: 93 percent / PPTS / CH2Cl2 / 7 h
7: 42 percent / acetic acid; tetrahydrofuran / 48 h / -10 °C
8: pyridine / 3 h / 0 °C
9: KH / diethyl ether; methanol / 0.33 h / 0 °C
10: 1.) n-BuLi / 1.) THF, -20 deg C, 2h, 2.) 9 h
11: 69 percent / NBS, AgNO3, 2,6-lutidine / H2O; acetonitrile / 0.12 h
12: LiAlH4, LiI / diethyl ether / 30 h / -100 °C
13: 88 percent / PPTS / CH2Cl2 / 7 h
With
pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; pyridinium p-toluenesulfonate; potassium hydride; potassium carbonate; silver nitrate; lithium iodide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; acetonitrile;
DOI:10.1016/S0040-4039(00)82885-3