5-Chloro-1-indanone → HCID 58392088, Verbindung

HRID 561443

Reaktionsgleichung

Reaktionsgleichung von HRID 561443
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10]2.[Cl:17][C:18]1[CH:26]=[C:25]2[C:21]([CH2:22][CH2:23][C:24]2=[O:27])=[CH:20][CH:19]=1>O1CCCC1.C(OCC)C>[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12]([CH:1]1[CH2:3][CH2:2]1)([OH:16])[CH2:11][CH2:10]2.[Cl:17][C:18]1[CH:26]=[C:25]2[C:21]([CH2:22][CH2:23][C:24]2([CH:1]2[CH2:3][CH2:2]2)[OH:27])=[CH:20][CH:19]=1

Komponenten

7

Edukt 3

HCID 1425995-Chloro-1-indanoneHCID 51007056-Chloro-1-indanoneHCID 178418630HCID 178418630, Verbindung

Produkt 2

HCID 58392088HCID 58392088, VerbindungHCID 58392268HCID 58392268, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

45 ml (22.5 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran were added to 2.50 g (15.0 mmol) of a mixture of 5-chloro-2,3-dihydro-1H-inden-1-one and 6-chloro-2,3-dihydro-1H-inden-1-one in 56 ml of diethyl ether at RT, and the mixture was stirred at RT overnight. The reaction mixture was added to ice-water, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) and preparative HPLC (mobile phase: acetonitrile/water gradient) to result in 71.0 mg (2% of theory) of a mixture of 5-chloro-1-cyclopropyl-2,3-dihydro-1H-inden-1-ol and 6-chloro-1-cyclopropyl-2,3-dihydro-1H-inden-1-ol.

Aufarbeitung

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) and preparative HPLC (mobile phase: acetonitrile/water gradient)

Quellen und Nachweise

ORD-Eintrag
ord-7475267fb2554cbbba68f9a98a747938
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

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