Réaction #9339

Équation de réaction

NaHCO3

DDQ

15-5

(Z)-7-{(1R,2S,3R)-3-Hydroxy-2-[1-(4-methoxy-benzyloxy)-indan-5-yl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

water

→

15-6

(Z)-7-[(1R,2S,3R)-3-Hydroxy-2-(1-hydroxy-indan-5-yl)-5-oxo-cyclopentyl]-hept-5-enoic acid methyl ester

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Extractionthe resulting mixture was extracted with dichloromethane (3×50 mL)
2. 2
   LavageThe combined dichloromethane solution was washed with brine
3. 3
   Séchagewas dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated
6. 6
   AutrePurification by flash chromatography on silica gel (50%→60% ethyl acetate/hexanes)

Mode opératoire

DDQ (41 mg, 0.18 mmol) was added to a mixture of 15-5 (11 mg, 0.021 mmol) in dichloromethane (3.5 mL)/water (175 μL). After 55 min., saturated NaHCO3 solution was added and the resulting mixture was extracted with dichloromethane (3×50 mL). The combined dichloromethane solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (50%→60% ethyl acetate/hexanes) gave 15-6 (34 mg, 60%).

Source