Multi-step reaction with 12 steps
1.1: 94 percent / toluenesulfonic acid / toluene / Heating
2.1: 100 percent / hydrogen / platinum(IV) oxide / ethyl acetate / 4.5 h
3.1: nitrogen tetroxide / acetonitrile / 1.25 h / -20 °C
4.1: sodium iodide / acetonitrile / -20 - 20 °C
5.1: 92 percent / trifluoroacetic acid / CH2Cl2 / 23 h / 20 °C
6.1: 72 percent / nitric acid / 3.5 h / 0 °C
7.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C
7.2: 82 percent / tetrahydrofuran / 2 h / -78 - 0 °C
8.1: 85 percent / iron; acetic acid / ethanol / 4.5 h / Heating
9.1: 87 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 - -60 °C
10.1: 98 percent / lithium hydroxide / methanol; H2O / 36 h / 20 °C
11.1: 70 percent / n-butyllithium; triethyamine; trimethylacetyl chloride / hexane; tetrahydrofuran / -78 - 20 °C
12.1: 89 percent / sulfuric acid / dioxane / 0.5 h / 20 °C
With
lithium hydroxide; n-butyllithium; sulfuric acid; o-toluenesulfonic acid; hydrogen; nitric acid; sodium hexamethyldisilazane; pivaloyl chloride; dinitrogen tetraoxide; iron; acetic acid; triethylamine; trifluoroacetic acid; sodium iodide;
platinum(IV) oxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; toluene; acetonitrile;
7.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1071/CH06324