Multi-step reaction with 13 steps
1: 1.) LDA, 2.) hexamethylphosphoramide / 1.) THF, -78 deg C, 1 h; 2.) THF, -78 deg C to room temperature, 15 h
2: 94 percent / lithium aluminium hydride / diethyl ether / 1.5 h / 0 °C
3: 85 percent / sodium hydride / dimethylformamide / 12 h / 0 - 20 °C
4: zirconiumbis(cyclopentadienyl) dichloride, n-Bu-Li
5: triethylamine / CH2Cl2 / 1 h / -5 °C
6: 15.84 g / sodium iodide / acetone / 15 h / Ambient temperature
7: 1.) THF, -78 deg C to room temp., 15 h; 2.) toluene, 3 h, reflux
8: 97 percent / di-isobutylaluminum hydride / toluene / 1 h / -78 - -30 °C
9: 99 percent / triethylamine / tetrahydrofuran / 1 h / -20 - 20 °C
10: 94 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / 0 °C
11: 97 percent / anhydrous potassium carbonate / methanol / 1 h / 0 °C
12: 79 percent / stannic chloride / tetrahydrofuran / 0.58 h / Ambient temperature
13: 95 percent / 2,6-dimethylpyridine / CH2Cl2 / 0.33 h / -20 °C
With
2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; zirconocene dichloride; diisobutylaluminum hydride; tin(IV) chloride; sodium hydride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;