反応 #2025293

反応方程式

(+)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine

N,N'-dicyclohexylcarbodiimide

4-pyrrolidinopyridine

dodecanic acid

→

(+)-2-{4-(1-dodecanoyloxyethyl)phenyl}-5-decyloxypyrimidine

収率 94.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他After completion of the reaction
2. 2
   ろ過the precipitates were filtered off
3. 3
   workup.ADDITION200 ml of toluene were added
4. 4
   洗浄by washing with water, 5% acetic acid, water, 5% aqueous sodium hydrogen carbonate solution and water in this order
5. 5
   乾燥After the organic phase was dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   その他The resulting residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate)

実験手順

Into 20 ml of dichloromethane were dissolved 1.78 g (5 millimoles) of the (+)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine obtained in Preparation Example [starting material compound (VI)] 70 and 1.2 g (6 millimoles) of dodecanic acid, and then 1.4 g of N,N'-dicyclohexylcarbodiimide and 0.1 g of 4-pyrrolidinopyridine were added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the precipitates were filtered off and 200 ml of toluene were added thereto, followed by washing with water, 5% acetic acid, water, 5% aqueous sodium hydrogen carbonate solution and water in this order. After the organic phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate) to obtain 2.53 g (yield: 94%) of (+)-2-{4-(1-dodecanoyloxyethyl)phenyl}-5-decyloxypyrimidine. The physical values are shown in Table-1.

出典