Multi-step reaction with 15 steps
1.1: 80 percent / lithium aluminium hydride / tetrahydrofuran / 1 h / Heating
2.1: 81 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / Heating
3.1: 93 percent / lithium hexamethyldisilazide / tetrahydrofuran / 16 h / 20 °C
4.1: 88 percent / hydrogen / palladium on charcoal / ethanol; methanol
5.1: 97 percent / p-toluenesulfonic acid monohydrate / tetrahydrofuran; methanol; H2O / 4.5 h / Heating
6.1: 92 percent / aq. sodium hydroxide; cetrimide; p-toluenesulfonyl chloride / CH2Cl2 / 0.5 h
7.1: magnesium / tetrahydrofuran / 2 h / Heating
7.2: 64 percent / copper iodide / tetrahydrofuran / 3 h / -30 °C
8.1: 100 percent / sodium hydride / tetrahydrofuran; various solvent(s) / 16 h / 20 °C
9.1: 95 percent / p-toluenesulfonic acid monohydrate / tetrahydrofuran; methanol; H2O / 0.5 h / Heating
10.1: 83 percent / pyridinium chlorochromate / CH2Cl2 / 0.75 h / Heating
11.1: 87 percent / lithium hexamethyldisilazide / tetrahydrofuran / 16 h / 20 °C
12.1: 100 percent / hydrogen / palladium on charcoal / ethanol
13.1: 95 percent / potassium hydroxide / methanol; tetrahydrofuran / 3 h / 40 °C
14.1: 76 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 / 1 h / 0 °C
15.1: 99 percent / potassium carbonate / acetone / 18 h / 20 - 40 °C
With
potassium hydroxide; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; hydrogen; cetyltrimethylammonim bromide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; magnesium; p-toluenesulfonyl chloride; triphenylphosphine; pyridinium chlorochromate; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;
3.1: Julia-Kocienski reaction / 11.1: Julia-Kocienski reaction;
DOI:10.1016/j.tet.2007.01.007