Multi-step reaction with 13 steps
1: 1.) NaH / 1.)THF, 1 h, reflux, 2.) 1 h, r.t.
2: 1.) CuI / 1.) ether, 10 min, -10 deg C, 2.) ether, -78 deg C, 1 h, -20 deg C, 16 h
3: 91 percent / diisobutylaluminium hydride (DIBAL) / toluene / 1 h / -78 °C
4: 1.) methanesulfonyl chloride, triethylamine, 2.) LiBr / 1.) dichloromethane, -78 deg C, 30 min, 2.) THF, -20 deg C, 1 h
6: 79 percent / stannic chloride / CH2Cl2; H2O / 1.) 0 deg C, 1 h, 2.) r.t., 20 h
7: 1.) NaH / 1.) THF, 1 h, reflux, 2.) 1 h, r.t.
8: 1.) CuI / 1.) ether, 10 min, -10 deg C, 2.) ether, -78 deg C, 1 h -> -20 deg C, 16 h
9: 95 percent / diisobutylaluminium hydride (DIBAL) / toluene / 1 h / -78 °C
10: 1.) methaneslfonyl chloride, triethylamine, 2.) LiBr / 1.) dichloromethane, -78 deg C, 30 min, 2.) THF, -20 deg C, 1 h
12: 81 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.17 h / -20 °C
13: 1.) BBr3, 2.) H2O / 1.) CH2Cl2, -78 deg C -> -10 deg C, 3 h, 2.) r.t., 12 h
With
3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; copper(l) iodide; water; boron tribromide; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; lithium bromide;
tin(IV) chloride;
In
dichloromethane; water; toluene;