Reaction #9340

Reaction equation

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

dichloroethane

→

15-8

Yield 64.3%

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

Yield 64.3%

Solvents

dichloromethane

water

Conditions

Workup

1. 1
   Extractionthe resulting mixture was extracted with dichloromethane (3×20 mL)
2. 2
   WashThe combined dichloromethane solution was washed with brine
3. 3
   Dryingwas dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated
6. 6
   OtherPurification of the residue by flash chromatography on silica gel (60% ethyl acetate/hexanes)

Procedure

DDQ (10 mg, 0.041 mmol) was added to a mixture of 15-5 (11 mg, 0.021 mmol) in dichloromethane (0.5 mL)/water (25 μL). After 1 h, dichloroethane (0.5 mL) was added and the reaction was stirred overnight. Saturated NaHCO3 solution was added and the resulting mixture was extracted with dichloromethane (3×20 mL). The combined dichloromethane solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (60% ethyl acetate/hexanes) gave 15-8 (5 mg, 59%).

Source