Multi-step reaction with 11 steps
1: 90 percent / potassium carbonate / acetone / 16 h / 20 °C
2: 89 percent / ammonium molybdate(VI) tetrahydrate; aq. hydrogen peroxide / tetrahydrofuran; various solvent(s) / 2 h / 20 °C
3: 91 percent / lithium hexamethyldisilazide / tetrahydrofuran / 16 h / 20 °C
4: 93 percent / hydrogen / palladium on charcoal / ethanol
5: 98 percent / potassium hydroxide / methanol; tetrahydrofuran / 3 h / 40 °C
6: 85 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 / 1 h / 20 °C
7: 91 percent / potassium carbonate / acetone / 18 h / 20 °C
8: 82 percent / ammonium heptamolybdate(VI) tetrahydrate; aq. hydrogen peroxide / tetrahydrofuran; various solvent(s) / 1 h / 20 °C
9: 74 percent / lithium hexamethyldisilazide / tetrahydrofuran / 2 h / 20 °C
10: 80 percent / 2,4,6-triisopropyl sulfonylhydrazide / tetrahydrofuran / 52 °C
11: 88 percent / potassium carbonate / tetrahydrofuran; acetone / 21 h / 20 - 40 °C
With
potassium hydroxide; N-Bromosuccinimide; ammonium molybdate tetrahydrate; ammonium molybdate tetrahydrate; 2,4,6-triisopropyl sulfonylhydrazide; hydrogen; dihydrogen peroxide; potassium carbonate; triphenylphosphine; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; acetone;
3: Julia-Kocienski reaction / 9: Julia-Kocienski reaction;
DOI:10.1016/j.tet.2007.01.007