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HRID 9244Erstellt: 23. Oktober 2026

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

https://huagongshe.com/de/reaction/9244

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt1,1-DichloroethaneHCID 6365—
Edukt2,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 6775—
EduktSodium BicarbonateHCID 516892—
Edukt(Z)-7-{(1R,2S,3R)-3-Hydroxy-2-[1-(4-methoxy-benzyloxy)-indan-5-yl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl esterHCID 69595718—
LösungsmittelWaterHCID 962—
LösungsmittelDichloromethaneHCID 6344—
Produkt(Z)-7-[(1R,2S,3R)-3-Hydroxy-5-oxo-2-(1-oxo-indan-5-yl)-cyclopentyl]-hept-5-enoic acid methyl esterHCID 1195533764,3%

Reaktionsschritte

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%).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07091231B2
Quelldatensatzuspto-grants-2006_08
ORD IDord-aab96c42632a4a4890d68c2d0cb345b0
Quellennotizuspto-grants-2006_08