반응 #2025293

반응 방정식

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

N,N'-dicyclohexylcarbodiimide

4-pyrrolidinopyridine

dodecanic acid

→

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

수율 94.0%

용매

dichloromethane

반응 조건

후처리

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

실험 절차

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.

출처