Multi-step reaction with 8 steps
1: 1) dibutyltin oxide, 2) Bu4NI / 1) benzene, 5 h, reflux, 2) 5 h, reflux
2: 1.5M H2SO4 / dioxane / 3 h / 100 °C
3: pyridine, 4-dimethylaminopyridine / 24 h
4: 1.95 g / tributyltin ethoxide / 1,2-dichloro-ethane / 3 h / Heating
5: 93 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 0.5 h / Ambient temperature
6: 70 percent / BF3*Et2O, 4A molecular sieves / CH2Cl2 / 0.5 h / 0 °C
7: 94 percent / NaOMe / methanol / 2 h / Ambient temperature
8: 93 percent / NaH / tetrahydrofuran / 3 h / Ambient temperature
With
pyridine; dmap; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; tributyltin ethoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane;