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Hydrochloric Acid → Methyl {[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-1H-inden-5-yl]oxy}acetate

HRID 569300
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 569300
[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[C:10]([Cl:18])[C:11]([Cl:17])=[C:12]([OH:16])[CH:13]=2)[C:8]1=[O:19])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29].Cl>CN(C)C=O.O>[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[C:10]([Cl:18])[C:11]([Cl:17])=[C:12]([O:16][CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:13]=2)[C:8]1=[O:19])(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 140981552-(Acetoxyethyl)-6,7-dichloro-2,3-dihydro-5-hydroxy-1H-inden-1-one

Produkt 1

HCID 14098156Methyl {[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-1H-inden-5-yl]oxy}acetateAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-(Acetoxyethyl)-6,7-dichloro-2,3-dihydro-5-hydroxy-1H-inden-1-one (5.8 gm, 0.0191 mole), potassium carbonate (3.97 gm, 0.0287 mole), methyl bromoacetate (3.52 gm, 0.023 mole) in dry N,N-dimethylformamide (35 ml) were stirred and heated at 60° C. for 3 hours. The mixture was cooled and poured into a mixture of water and ice containing hydrochloric acid. The resulting mixture was extracted with a mixture of ether and tetrahydrofuran then methylene chloride. The combined organic extracts were washed with water, then with brine and finally dried over MgSO4. Evaporation of the solvent gave 6.9 gm of residue which was purified by column chromatography using silica (300 gm) and eluting with a 50/1 mixture of methylene chloride and tetrahydrofuran. Combining the appropriate fractions and evaporating the solvent gave 3.3 gm of product, m.p. 111°-113° C.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionThe resulting mixture was extracted with a mixture of ether and tetrahydrofuran
  3. washThe combined organic extracts were washed with water
  4. dry with materialwith brine and finally dried over MgSO4
  5. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-7aaa239ebc3f4844824e6eaeac4ab07b
Quelldatensatz
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04731471

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