反应详情

温度

40 °C

0.7 ml of concentrated aqueous hydrochloric acid was dropped, whilst ice-cooling, into a solution of 500 mg of 2-(4-aminophenoxymethyl)-2-methylchroman (prepared as described in Preparation 4) in 5 ml of acetone, and then a solution of 170 mg of sodium nitrite in 2 ml of water was added dropwise to the resulting mixture. When the dropwise additon was complete, 2 ml of ethyl acrylate were added, and the reaction mixture was heated to 40° C. 10 mg of cuprous oxide were then added gradually, and the mixture was stirred for 30 minutes. At the end of this time, the acetone was distilled off under reduced pressure, and the residue was extracted with benzene. The benzene extract was dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was subjected of silica gel column chromatography eluted with a 10:1 dy volume mixture of hexane and ethyl acetate, to afford 350 mg of the title compound as a pale yellow oily substance.

1. distillationAt the end of this time, the acetone was distilled off under reduced pressure
2. extractionthe residue was extracted with benzene
3. extractionThe benzene extract
4. dry with materialwas dried over anhydrous magnesium sulfate
5. distillationThe solvent was then distilled off under reduced pressure
6. washeluted with a 10:1 dy volume mixture of hexane and ethyl acetate