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Imidazole → 3-Imidazol-1-yl-2,2-dimethyl-indan-1-one

HRID 1690771
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1690771
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(N(C(C)C)CC)(C)C.O[CH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28](=[O:35])[C:27]1([CH3:37])[CH3:36].[NH:38]1[CH:42]=[CH:41][N:40]=[CH:39]1>ClCCl.C([O-])(O)=O.[Na+].C(OCC)(=O)C>[N:38]1([CH:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28](=[O:35])[C:27]2([CH3:37])[CH3:36])[CH:42]=[CH:41][N:40]=[CH:39]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 795ImidazoleHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 130236813-Hydroxy-2,2-dimethyl-1-indanone

Produkt 1

HCID 577810843-Imidazol-1-yl-2,2-dimethyl-indan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344
Dichloromethane
Lösungsmittel
3×
HCID 8857Ethyl AcetateLösungsmittel
HCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of trifluoromethansulfonic anhydride (1.13 mL, 6.75 mmol) in dichloromethane (10 mL) at −78° C. is added, via cannula, a solution of diisopropylethylamine (1.8 mL, 10.1 mmol) and 3-hydroxy-2,2-dimethyl-indan-1-one, prepared as described in Example 8c, (400 mg, 2.25 mmol) in dichloromethane (5 mL). The reaction is stirred at −78° C. for 10 min and then is placed at −10° C. for 10 min. The reaction is then re-cooled to −7.8° C. and a solution of imidazole (920 mg, 13.5 mmol) in dichloromethane (12 mL) is added via cannula. The reaction is then placed at room temperature for 1 h, at which time it is diluted with saturated aqueous NaHCO3 and ethyl acetate. The layers are separated and the aqueous layer is extracted twice with ethyl acetate. The combined organic layers are dried with MgSO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 1:3 to 1:0) to afford 3-imidazol-1-yl-2,2-dimethyl-indan-1-one; MS (ESI) m/z 227 (M+H)+; 1H NMR: (400 MHz, CHLOROFORM-d) δ ppm 0.80 (s, 3 H), 1.41 (s, 3 H), 5.52 (s, 1 H), 6.73 (s, 1 H), 7.12 (s, 1 H), 7.51 (d, J=7.6 Hz, 1 H), 7.56 (s, 1 H), 7.62 (t, J=7.5 Hz, 1 H), 7.70-7.80 (m, 1 H), 7.91 (d, J=7.6 Hz, 1 H).

Aufarbeitung

  1. waitis placed at −10° C. for 10 min
  2. temperatureThe reaction is then re-cooled to −7.8° C.
  3. waitThe reaction is then placed at room temperature for 1 h, at which time it
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted twice with ethyl acetate
  6. dry with materialThe combined organic layers are dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 1:3 to 1:0)

Quellen und Nachweise

ORD-Eintrag
ord-170669b926684ab1a049c2bdd1f28604
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08153674B2

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