Multi-step reaction with 10 steps
1.1: toluene / 1.17 h / 60 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 2.25 h / -30 - 50 °C
2.2: 2 h / 60 °C
3.1: sodium hydroxide / tetrahydrofuran / 2.5 h / 50 °C
4.1: N,N-dimethyl-formamide; oxalyl dichloride / chloroform / 1.17 h / 0 °C
5.1: tetrahydrofuran; acetonitrile; dichloromethane / 3 h / 0 °C
6.1: silver(I) acetate / 1,4-dioxane; water / 0.75 h / 60 °C
7.1: dichloromethane; methanol / 0.33 h
8.1: trifluoroacetic acid / chloroform / 3.5 h / 0 - 20 °C
9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / chloroform / 20 °C
10.1: sodium hydroxide / tetrahydrofuran / 2.5 h / 0 - 20 °C
With
oxalyl dichloride; silver(I) acetate; sodium hexamethyldisilazane; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; toluene; acetonitrile;
6.1: |Wolff Rearrangement;
DOI:10.1248/cpb.c13-00980