Reacción #63768

Ecuación de reacción

acetic acid

4-(3-t-butyldimethylsilyloxy-3-cyclopentyl-1-propenyl)-5-(1-hydroxy-6-methoxycarbonyl-2-hexyn-1-yl)-2-cyclopentenone

sodium bicarbonate

tetrahydrofuran

→

4-(3-hydroxy-3-cyclopentyl-1-propenyl)-5-(1-hydroxy-6-methoxycarbonyl-2-hexyn-yl)-2-cyclopentenone

Rendimiento 79.3%

Disolventes

water

—

mixed solvent

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextraction
2. 2
   Lavadowashed with a saturated aqueous solution of sodium chloride
3. 3
   Secadodried over anhydrous sodium sulfate
4. 4
   FiltraciónThe dried product was filtered
5. 5
   Concentraciónconcentrated

Procedimiento

63 mg (0.133 mmole) of 4-(3-t-butyldimethylsilyloxy-3-cyclopentyl-1-propenyl)-5-(1-hydroxy-6-methoxycarbonyl-2-hexyn-1-yl)-2-cyclopentenone obtained in Example 25 was dissolved in 2 ml of a mixed solvent composed of acetic acid, tetrahydrofuran and water in a ratio of 3:2:2, and the solution was stirred for 20 hours. An aqueous solution of sodium bicarbonate and ethyl acetate were added to the reaction mixture to perform extraction. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The dried product was filtered, concentrated and subjected to silica gel column chromatography (silica gel 5 g; eluent, hexane:ethyl acetate=5:1→1:1) to give 38 mg (yield 79%) of 4-(3-hydroxy-3-cyclopentyl-1-propenyl)-5-(1-hydroxy-6-methoxycarbonyl-2-hexyn-yl)-2-cyclopentenone. The resulting compound had the following spectral data.

Fuente