Multi-step reaction with 13 steps
1: 67 percent / o-xylene / 0.42 h / 170 °C
2: 94 percent / sodium hydride / dimethylformamide / 12 h / 20 °C
3: 93 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating
4: 86 percent / MnO2 / CH2Cl2 / 72 h / 20 °C
5: 85 percent / Na / ethanol / 72 h / -15 °C
6: 82 percent / CH2Cl2 / 24 h / 20 °C
7: 70 percent / Bu4NF/SiO2 / 0.03 h / microwave irradiation
8: 97 percent / tetrahydrofuran / 24 h / 50 °C
9: 95 percent / LiOH*H2O / tetrahydrofuran; H2O / 2 h / 20 °C
10: 62 percent / tetrahydrofuran; diethyl ether / 2 h / -15 °C
11: 84 percent / dimethylformamide / 80 °C
12: 90 percent / K2CO3 / 2-methoxy-ethanol / 24 h / Heating
13: 83 percent / sodium thiomethoxide / dimethylformamide / 3 h / 80 °C
With
manganese(IV) oxide; lithium hydroxide; lithium aluminium tetrahydride; sodium thiomethoxide; tetrabutyl ammonium fluoride; sodium; silica gel; sodium hydride; potassium carbonate;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 2-methoxy-ethanol; o-xylene; water; N,N-dimethyl-formamide;
6: Staudinger reaction;
DOI:10.1021/jo026508x