Multi-step reaction with 10 steps
1: 72 percent / diethyl ether / 20 h / Heating
2: 93 percent / p-TsOH / dimethylformamide / 0.5 h / Ambient temperature
3: 96 percent / DMAP / ethyl acetate / 1.5 h / Ambient temperature
4: H2 / palladium black / methanol / 0.17 h / Ambient temperature
5: pyridine / 1 h / Ambient temperature
6: 958 mg / CH3ONa / CHCl3; methanol / 20 h / 0 °C
7: 1.) BuLi / 1.) THF, hexane, -20 deg C, 2 h, 2.) THF, hexane, -20 deg C, 2 h, then 0-2 deg C, 4 d
8: 1.) NaH / 1.) DMF, RT, 0.5 h, 2.) DMF, RT, 0.5 h
9: HgO, HgCl2 / acetone; H2O / 0.33 h / 70 °C
10: 1.) BuLi / 1.) ether, hexane, -78 deg C, 1.5 h, 2.) ether, hexane, -78 to 0 deg C, 1.5 h
With
pyridine; dmap; n-butyllithium; hydrogen; sodium methylate; sodium hydride; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide;
palladium;
In
methanol; diethyl ether; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1246/bcsj.54.1749