Multi-step reaction with 21 steps
1: 91 percent / benzene / 20 h / Heating
2: 95 percent / 90percent aq. CF3COOH / 0.25 h / 25 °C
3: 84 percent / AcOK / 0.08 h / Heating
4: 94 percent / diisobutylaluminium hydride / tetrahydrofuran / -10 °C
5: 82 percent / K2CO3 / dimethylformamide / 96 h / 25 °C
6: 90 percent / MnO2 / CH2Cl2 / 12 h / 25 °C
7: p-ClC6H4CO3H / CH2Cl2 / 72 h / Heating
8: NaOMe, MeOH / 0.08 h
9: K2CO3 / dimethylformamide / 72 h / 50 °C
10: 95 percent / dimethylformamide / 12 h / Heating
11: 85 percent / NaOH / methanol; H2O / 96 h / Heating
12: (COCl)2 / CH2Cl2 / 2.5 h / 25 °C
13: CH2Cl2 / 2 h / 25 °C
14: SOCl2 / CH2Cl2 / 2 h / 25 °C
15: 88 percent / tetrahydrofuran / 0.75 h / 25 °C
16: 1.) BuLi, TMEDA / 1.) THF, -78 deg C, 1 h
17: HCl / dioxane / 0.5 h / Heating
18: 99 percent / LiAlH4 / tetrahydrofuran / 2 h / 25 °C
19: 80 percent / H2, Et3N, (CF3CO)2O / Pd/C / tetrahydrofuran / 18 h
20: 1.) BCl3, 2.) KOH, air / 1.) CH2Cl2, -10 deg C, 8 h, 2.) EtOH/EtOAc, 30 s
21: KHCO3 / dimethylformamide / 8 h
With
hydrogenchloride; methanol; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; oxalyl dichloride; air; N,N,N,N,-tetramethylethylenediamine; p-chloroperbenzoic acid; hydrogen; sodium methylate; potassium acetate; boron trichloride; diisobutylaluminium hydride; potassium carbonate; potassium hydrogencarbonate; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1039/c39910000190