Multi-step reaction with 10 steps
1.1: phosphorus oxychloride / 24 h / 170 °C / 17065.9 Torr
2.1: sulfuric acid / 2 h / 120 °C
3.1: 98.1 percent / sodium nitrite; acetic acid; acetic anhydride / 20 °C
4.1: oxalyl chloride; N,N-dimethylformamide / CH2Cl2 / 4 h / 20 °C
5.1: magnesium chloride; triethylamine / acetonitrile / 2 h / 20 °C
5.2: 86.7 percent / acetonitrile; CH2Cl2 / 20 °C
6.1: acetic anhydride / 2 h / 130 °C
7.1: tetrahydrofuran / 1 h / 20 °C
8.1: sodium hydride / tetrahydrofuran / 0 - 20 °C
9.1: 45.3 percent / N,N-diisopropylethylamine / acetonitrile / 20 °C
10.1: 75 percent / lithium hydroxide / dioxane; H2O / 48 h / 20 °C
With
lithium hydroxide; oxalyl dichloride; sulfuric acid; acetic anhydride; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; magnesium chloride; sodium nitrite; trichlorophosphate;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;
DOI:10.1021/ol0481378