反応 #66730
ord-5ce4ea56a24644e28963542948ca5db0
反応方程式
反応条件
後処理
- 1その他the mixture was put into a preheated bath at 90° C
- 2温度The mixture was heated until gas evolution
- 3その他(ca. 1.5 h)
- 4その他was continued at 100° C
- 5温度it was cooled to room temperature
- 6抽出the mixture was extracted twice with 1M aqueous sodium carbonate solution
- 7抽出The aqueous layer was extracted with ethyl acetate
- 8乾燥the combined organic layer was dried over sodium sulphate
- 9その他evaporated
実験手順
0.7 g of 4-Oxo-adamantane-1-carboxylic acid (11) were codistilled twice with toluene and dissolved in 5.5 mL of dry toluene. 1.1 mL of triethylamine were added. At 0° C., 0.9 mL of diphenylphosphoryl azide were added dropwise. The mixture was allowed to warm to room temperature and then the mixture was put into a preheated bath at 90° C. The mixture was heated until gas evolution ceased (ca. 1.5 h). 1.9 mL of benzyl alcohol were added and stirring was continued at 100° C. When the reaction was complete, it was cooled to room temperature, then ethyl acetate was added and the mixture was extracted twice with 1M aqueous sodium carbonate solution. The aqueous layer was extracted with ethyl acetate and the combined organic layer was dried over sodium sulphate and evaporated. The resulting oil was subjected to silica gel chromatography (heptanes:ethyl acetate) to give 871 mg of the desired product. Rt=1.40 min (Method 3). Detected mass: 300.2 (M+H+).