반응 #2025283

반응 방정식

butyrylchloride

(+)-3-methyl-3-(4-benzyloxyphenyl)propanol

water

→

(+)-4-benzyloxy-1-(1-methyl-3-butyryloxypropyl)benzene

수율 95.0%

용매

pyridine

반응 조건

후처리

1. 1
   기타reacted for 2 hours
2. 2
   추출extracted with 200 ml of toluene
3. 3
   기타separated
4. 4
   세척washed with, in the order, 1N aqueous solution of hydrochloric acid, water, 5% aqueous solution of sodium bicarbonate and water
5. 5
   건조dried on anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONAfter the solvent was distilled out under the reduced pressure
7. 7
   기타the resulting residue was purified by silica gel column chromatography (eluent: toluene-ethyl acetate)

실험 절차

2.56 (10 millimols) of (+)-3-methyl-3-(4-benzyloxyphenyl)propanol (XI-1) obtained in Preparation Example (starting material compound (V)) 1, was dissolved in 20 ml of pyridine and 1.38 g (13 millimols) of butyrylchloride was added at 30°-40° C. and reacted for 2 hours. The reaction mixture was poured into 200 ml of water and extracted with 200 ml of toluene and separated and then washed with, in the order, 1N aqueous solution of hydrochloric acid, water, 5% aqueous solution of sodium bicarbonate and water, and thereafter dried on anhydrous magnesium sulfate. After the solvent was distilled out under the reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: toluene-ethyl acetate) to provide 3.1 g (yield: 95%) of (+)-4-benzyloxy-1-(1-methyl-3-butyryloxypropyl)benzene (VIII-9).

출처