aluminium Etherification; 48 h; Heating;

1: 11.31 g / diphenyl carbonate; sodium hydrogen carbonate / N,N-dimethyl-acetamide / 5 h / 100 °C 2: 91 percent / aluminium / 48 h / Heating View Scheme

1: With N-methyl-pyrrolidine; chloro-trimethyl-silane in acetonitrile T=20°C; 1 h; 2: With trifluoroacetic anhydride in acetonitrile T=0°C; 0.0833333 h; 3: With 4-nitro-phenol; anhydrous sodium hydrogen carbonate; ammonia; water more than 3 stages;

chloro-trimethyl-silane; ammonia; trifluoroacetic anhydride in 1,4-dioxane; ethanol; acetonitrile

1.1: 86 percent / imidazole / dimethylformamide / 12 h / 20 °C 2.1: aq. Na2CO3; tetrabutylammonium bromide; 2,4,6-triisopropylbenzenesulfonyl chloride / CH2Cl2 / 20 °C 2.2: 89 percent / Et3N; 1,4-diazabicyclo[2,2,2]octane / acetonitrile / 3 h / 20 °C 3.1: Lawesson's reagent / toluene / 2 h / Heating 4.1: 78 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / 20 h / 20 °C 5.1: 80 percent / 1,1,3,3-tetramethylguanidine; syn-o-nitrobenzaldoxime / acetonitrile / 3 h / 20 °C View Scheme