Multi-step reaction with 8 steps
1: 1.) n-BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) THF, hexane, from -70 to 10 deg C
2: camphorsulfonic acid / toluene / 24 h / Heating
3: 29 percent / LiAlH4 / tetrahydrofuran / 2.5 h / Heating
4: 73 percent / imidazole / tetrahydrofuran / 1 h / Ambient temperature
5: 92 percent / pyridinium chlorochromate, molecular sieves / CH2Cl2 / 1 h / Ambient temperature
6: 98 percent / tetrahydrofuran / 0.17 h / -78 °C
7: pyridine, 4-(dimethylamino)pyridine / 2 h / Ambient temperature
8: Bu4NF, acetic acid / tetrahydrofuran / 2 h / 0 °C
With
pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; n-butyllithium; molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; acetic acid; pyridinium chlorochromate;
In
tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jm960301c