Toluene → 4-(4'-Chloro-4-ethylbiphenyl-3-yl)-2-methoxymethyl-2,6,6-trimethylpyran-3,5-dione

HRID 1470891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470891
[CH3:1][O:2][CH2:3][C:4]1([CH3:14])[C:9](=[O:10])[CH2:8][C:7](=[O:11])[C:6]([CH3:13])([CH3:12])[O:5]1.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][C:48]([CH2:51][CH3:52])=[C:47]([Pb+3])[CH:46]=2)=[CH:41][CH:40]=1>ClCCl.Cl>[Cl:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]2[CH:50]=[CH:49][C:48]([CH2:51][CH3:52])=[C:47]([CH:8]3[C:7](=[O:11])[C:6]([CH3:13])([CH3:12])[O:5][C:4]([CH2:3][O:2][CH3:1])([CH3:14])[C:9]3=[O:10])[CH:46]=2)=[CH:43][CH:44]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 6212ChloroformHCID 68488092HCID 68488092, VerbindungHCID 178476534HCID 178476534, Verbindung

Produkt 1

HCID 684861254-(4'-Chloro-4-ethylbiphenyl-3-yl)-2-methoxymethyl-2,6,6-trimethylpyran-3,5-dioneAusbeute 23,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 2-methoxymethyl-2,6,6-trimethylpyran-3,5-dione (0.141 g, 0.705 mmol) and N,N-dimethylaminopyridine (0.43 g, 3.52 mmol) in a mixed solvent system of anhydrous chloroform (7.5 ml) and anhydrous toluene (1.75 ml), is added 4′-chloro-4-ethylbiphenyl-3-yllead triacetate (0.465 g, 0.775 mmol) in one portion and the mixture heated at 80° C. for 2 hours. The mixture is allowed to cool to room temperature, diluted with dichloromethane and dilute aqueous hydrochloric acid, and stirred for 5 minutes then filtered through diatomaceous earth to remove inorganic residues (additional washing with solvents). The organic fractions are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel (hexane/ethyl acetate 4:1 ratio). Fractions containing the desired product are combined and evaporated in vacuo. Trituration with hexanes affords 4-(4′-chloro-4-ethylbiphenyl-3-yl)-2-methoxymethyl-2,6,6-trimethylpyran-3,5-dione (0.070 g) as a white solid.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationthen filtered through diatomaceous earth
  3. customto remove inorganic
  4. washresidues (additional washing with solvents)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is purified by column chromatography on silica gel (hexane/ethyl acetate 4:1 ratio)
  9. additionFractions containing the desired product
  10. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9547da9af3a2462a83f33a196cf64f31
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006429B2

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