Methanesulfonic Acid → 2-(4-Methoxy-3-methylphenyl)-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}ethanone

HRID 9667

Reaktionsgleichung

Reaktionsgleichung von HRID 9667
CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([OH:31])=O)=[CH:24][C:23]=1[CH3:32].[CH3:33][C:34]1[CH:35]=[C:36]([C:39]2[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=2)[S:37][CH:38]=1.C([O-])(O)=O.[Na+]>O>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([C:38]2[S:37][C:36]([C:39]3[CH:40]=[CH:41][C:42]([C:45]([F:46])([F:48])[F:47])=[CH:43][CH:44]=3)=[CH:35][C:34]=2[CH3:33])=[O:31])=[CH:24][C:23]=1[CH3:32]

Komponenten

7

Edukt 5

HCID 6395Methanesulfonic AcidHCID 14812Phosphorus oxide (P4O10)HCID 1382764-Methoxy-3-methylphenylacetic acidHCID 516892Sodium BicarbonateHCID 21986373Thiophene, 4-methyl-2-[4-(trifluoromethyl)phenyl]-2×

Produkt 1

HCID 219863702-(4-Methoxy-3-methylphenyl)-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To methanesulfonic acid (8 ml) in a flask under N2 was added P2O5 (0.56 g), the resulting suspension was heated to 60° C. until a clear solution formed. The mixture was cooled to room temperature prior to addition of 4-methoxy-3-methyl-phenylacetic acid (0.3549) and 4-methyl-2-[4-(trifluoromethyl)phenyl]thiophene (intermediate 102, 0.4 g). The mixture was then heated to 60° C. for 90 minutes. The reaction mixture was cooled to room temperature and then poured into iced water. The suspension was made basic by cautious addition of NaHCO3 and the products extracted into ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and evaporated to yield a brown oil. Purification by flash column chromatography eluting with 5% EtOAc/cyclohexane yielded the title compound as a brown gum.

Aufarbeitung

  1. customformed
  2. temperatureThe mixture was cooled to room temperature
  3. temperatureThe mixture was then heated to 60° C. for 90 minutes
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionthe products extracted into ethyl acetate
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto yield a brown oil
  10. customPurification by flash column chromatography
  11. washeluting with 5% EtOAc/cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-450d571946b54fa997b752c94963e482
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091237B2

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