Benzyl mercaptan → Ethyl 3-[(benzylthio)methyl]-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate

HRID 9644

Reaktionsgleichung

Reaktionsgleichung von HRID 9644
Br[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[S:5][C:4]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[CH2:23]([SH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:23]([S:30][CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[S:5][C:4]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 21986402Ethyl 3-(bromomethyl)-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate2×

Produkt 1

HCID 21986405Ethyl 3-[(benzylthio)methyl]-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of ethyl 3-(bromomethyl)-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate (intermediate 43, 0.100 g) and benzyl mercaptan (0.30 g) in acetonitrile (10 ml) was treated with potassium carbonate (0.46 g) and the mixture stirred at ambient temperature overnight. The reaction mixture was partitioned between ethyl acetate and water the organic layer as collected, dried over magnesium sulfate and concentrated. The residue was purified by SPE (Si cartridge) eluting initially with cyclohexane:chloroform (5:1) and then cyclohexane:chloroform (1:3) to give the title compound as a colourless oil.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water the organic layer
  2. customas collected
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by SPE (Si cartridge)
  6. washeluting initially with cyclohexane:chloroform (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-dd4a8782106f4e99b7bf266d0a434e30
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091237B2

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