Sodium Chloride → 2-{1-(4-Phenoxyphenyl)propan-1-ylidene}-1,3-dithiolan

HRID 2372427

Reaktionsgleichung

Reaktionsgleichung von HRID 2372427
C(OP([CH:9]1[S:13][CH2:12][CH2:11][S:10]1)(OCC)=O)C.CCCCCC.C([Li])CCC.[CH:25]1[CH:30]=[CH:29][C:28]([C:31]([CH2:33][CH2:34][O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=O)=[CH:27][CH:26]=1.[Cl-].[Na+]>O1CCCC1>[O:35]([C:34]1[CH:26]=[CH:27][C:28]([C:29](=[C:9]2[S:10][CH2:11][CH2:12][S:13]2)[CH2:30][CH3:25])=[CH:31][CH:33]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Komponenten

7

Edukt 5

HCID 5234Sodium ChlorideHCID 8058HexaneHCID 38763553-Phenoxy-1-phenylpropan-1-oneHCID 133020352-Diethoxyphosphoryl-1,3-dithiolaneHCID 178418339Butyllithium

Produkt 1

HCID 199043722-{1-(4-Phenoxyphenyl)propan-1-ylidene}-1,3-dithiolanAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-Diethoxyphosphoryl-1,3-dithiolan, 3.0 g, was dissolved in 30 ml of tetrahydrofuran and 7.75 ml of 1.6 mole hexane solution of n-butyl lithium was dropwise added to the solution in an argon flow at -65° C. The mixture was stirred at the same temperature for an hour. Then, a solution of 2.55 g of 4-phenoxypropiophenone in 9 ml of tetrahydrofuran was dropwise added to the mixture at the same temperature. The reaction mixture was gradually warmed to room temperature overnight. This suspension was poured onto saturated sodium chloride aqueous solution and the mixture was extracted with chloroform. After drying the chloroform phase over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform : hexane =1 : 1) to give 2.60 g of the product.

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialAfter drying the chloroform phase over magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform : hexane =1 : 1)

Quellen und Nachweise

ORD-Eintrag
ord-40b7a1c835c347f9958e3d3f188c45bc
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05098928

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