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

HRID 9243Notes

Reaction equation

HRID 9243 reaction equation
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[CH3:15][O:16][C:17](=[O:50])[CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][C@H:24]1[C:28](=[O:29])[CH2:27][C@@H:26]([OH:30])[C@@H:25]1[C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[CH:36]([O:40]CC1C=CC(OC)=CC=1)[CH2:35][CH2:34]2.O.C([O-])(O)=O.[Na+]>ClCCl>[CH3:15][O:16][C:17](=[O:50])[CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][C@H:24]1[C:28](=[O:29])[CH2:27][C@@H:26]([OH:30])[C@@H:25]1[C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[CH:36]([OH:40])[CH2:35][CH2:34]2

Participants

6

Reactant 4

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 69595718(Z)-7-{(1R,2S,3R)-3-Hydroxy-2-[1-(4-methoxy-benzyloxy)-indan-5-yl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

Product 1

HCID 11955336(Z)-7-[(1R,2S,3R)-3-Hydroxy-2-(1-hydroxy-indan-5-yl)-5-oxo-cyclopentyl]-hept-5-enoic acid methyl esterYield 434.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane (3×50 mL)
  2. washThe combined dichloromethane solution was washed with brine
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography on silica gel (50%→60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-499c1cc00a404c2bb82dd402c8304336
Source dataset
uspto-grants-2006_08
Patent number
US07091231B2

Reaction notes

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