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Diethyl Ether → HCID 19024388, Verbindung

HRID 1033731
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1033731
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][SH:12])=[CH:7][CH:6]=1.Br[C:14]([CH3:26])([CH3:25])[C:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24])=[O:16].C(OCC)C>C1COCC1.CCCCCC.O>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[C:15](=[O:16])[C:14]([S:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=1)([CH3:25])[CH3:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 152640192-Bromo-1-(2,4-difluorophenyl)-2-methyl-1-propanone

Produkt 1

HCID 19024388HCID 19024388, VerbindungAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

In 180 ml of THF was suspended 2.4 g (60 mmol) of 60% sodium hydride having been washed with hexane, and 9.4 g (61 mmol) of 4-methoxy-α-toluenethiol was added dropwise to the suspension while stirring under ice-cooling. After being stirred for 10 minutes, the mixture was added dropwise to a solution of 15.0 g (57 mmol) of 2-bromo-1-(2,4-difluorophenyl)-2-methylpropan-1-one in 225 ml of THF with stirring under ice-cooling. To the reaction mixture were added diethyl ether and water, and the organic layer was separated, washed with water and then with a saturated sodium chloride aqueous solution, and dried. The solvent was removed by distillation under reduced pressure, and the residue was subjected to column chromatography using a mixed solvent of hexane and ethyl acetate (10:1). The solvent was removed by distillation under reduced pressure to obtain 19.2 g (95%) of 1-(2,4-difluorophenyl)-2-((4-methoxyphenyl)methylthio)-2-methylpropan-1-one as a colorless oily substance.

Aufarbeitung

  1. additionwas added dropwise to the suspension
  2. temperaturecooling
  3. stirringAfter being stirred for 10 minutes
  4. stirringwith stirring under ice-
  5. temperaturecooling
  6. customthe organic layer was separated
  7. washwashed with water
  8. dry with materialwith a saturated sodium chloride aqueous solution, and dried
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3777a4e6c7f544be872e15e0a13c7ef1
Quelldatensatz
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05312815

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