Diisopropylamine → 5-Formyl-3-(2,2,2-trifluoroacetylamino)thiophene-2-carboxylic acid methyl ester

HRID 72238

Reaktionsgleichung

Reaktionsgleichung von HRID 72238
[Li]CCCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]([C:17]1[S:18][CH:19]=[CH:20][C:21]=1[NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])=[O:16].[CH:29](N1CCCCC1)=[O:30].[Cl-].[NH4+]>CCCCCC.C1COCC1>[CH3:13][O:14][C:15]([C:17]1[S:18][C:19]([CH:29]=[O:30])=[CH:20][C:21]=1[NH:22][C:23](=[O:28])[C:24]([F:25])([F:26])[F:27])=[O:16]

Komponenten

8

Edukt 5

HCID 7912DiisopropylamineHCID 174291-PiperidinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 2805185Methyl 3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylateHCID 178418339Butyllithium

Produkt 1

HCID 576187255-Formyl-3-(2,2,2-trifluoroacetylamino)thiophene-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 1.6M n-BuLi solution in hexane (12 mL) was added dropwise to a solution of diisopropylamine (2.9 mL) in THF (30 mL) at −78° C. The reaction mixture was stirred at 0° C. for 10 min and then cooled to −78° C., and a solution of 3-(2,2,2-trifluoroacetylamino)thiophene-2-carboxylic acid methyl ester (1.5 g) in THF (15 mL) was added. The reaction mixture was stirred at −78° C. for 30 min and then 1-formylpiperidine (4 g) was added, and the mixture was again stirred at this temperature for 1.5 h. Subsequently, saturated ammonium chloride solution was added and the reaction mixture was allowed to reach room temperature. The aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate and the solvent was removed in vacuo. The product with the molecular weight of 281.0 (C9H6F3NO4S) was obtained in this way; MS (ESI): 282 (M+H+).

Aufarbeitung

  1. temperaturecooled to −78° C.
  2. stirringThe reaction mixture was stirred at −78° C. for 30 min
  3. stirringthe mixture was again stirred at this temperature for 1.5 h
  4. customto reach room temperature
  5. extractionThe aqueous phase was extracted several times with ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. customthe solvent was removed in vacuo
  8. customThe product with the molecular weight of 281.0 (C9H6F3NO4S) was obtained in this way

Quellen und Nachweise

ORD-Eintrag
ord-063af6f49cc04f6fbaaa08dfff6a4a13
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828991B2

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