반응 #63767

반응 방정식

tetrahydrofuran

4-t-butyldimethyl silyloxy-3-(3-t-butyldimethylsilyloxy-1-octenyl)-2-(1-hydroxy-6-methoxycarbonylhexyl)cyclopentanone

sodium bicarbonate

acetic acid

→

4-(3-hydroxy-1-octenyl)-5-(1-hydroxy-6-methoxycarbonylhexyl)cyclopentenone

수율 62.0%

용매

—

mixed solvent

ethyl acetate

water

ethyl acetate

hexane

반응 조건

후처리

1. 1
   추출extraction
2. 2
   세척washed with a saturated aqueous solution of sodium chloride
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   여과The dried product was filtered

실험 절차

370 mg (60 mmoles) of 4-t-butyldimethyl silyloxy-3-(3-t-butyldimethylsilyloxy-1-octenyl)-2-(1-hydroxy-6-methoxycarbonylhexyl)cyclopentanone obtained in Example 22, (1) was dissolved in 10 ml of a mixed solvent consisting of acetic acid, tetrahydrofuran and water in a ratio of 2:1:1, and the solution was stirred at 80° C. for 7 hours. An aqueous solution of sodium bicarbonate and ethyl acetate were added to perform extraction. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The dried product was filtered, concentratd, and subjected to silica gel column chromatography (silica gel), 10 g; eluent, hexane:ethyl acetate=5:1→1:2) to give 218 mg (yield 62%) of 4-(3-hydroxy-1-octenyl)-5-(1-hydroxy-6-methoxycarbonylhexyl)cyclopentenone

출처