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

HRID 9244

Reaktionsgleichung

Reaktionsgleichung von HRID 9244
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.ClC(Cl)C.C([O-])(O)=O.[Na+]>ClCCl.O>[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)[C:36](=[O:40])[CH2:35][CH2:34]2

Komponenten

7

Edukt 4

HCID 63651,1-DichloroethaneHCID 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

Produkt 1

HCID 11955337(Z)-7-[(1R,2S,3R)-3-Hydroxy-5-oxo-2-(1-oxo-indan-5-yl)-cyclopentyl]-hept-5-enoic acid methyl esterAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with dichloromethane (3×20 mL)
  2. washThe combined dichloromethane solution was washed with brine
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification of the residue by flash chromatography on silica gel (60% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-aab96c42632a4a4890d68c2d0cb345b0
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091231B2

Verknüpfte Notizen

Wird geladen…