Water → Diethyl 2-((isopropyl)amino)thiophene-3,4-dicarboxylate

HRID 131574

Reaktionsgleichung

Reaktionsgleichung von HRID 131574
[CH2:1]([O:3][C:4]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])[CH3:2].[CH:26]([N:29]=[C:30]=[S:31])([CH3:28])[CH3:27].Br[CH2:33][C:34](=O)[C:35]([O:37][CH2:38][CH3:39])=[O:36].O>C1COCC1>[CH:26]([NH:29][C:30]1[S:31][CH:33]=[C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])([CH3:28])[CH3:27]

Komponenten

6

Edukt 4

HCID 962WaterHCID 66144Ethyl bromopyruvate2×HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 75263Isopropyl Isothiocyanate

Produkt 1

HCID 68818932Diethyl 2-((isopropyl)amino)thiophene-3,4-dicarboxylateAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Ethoxycarbonylmethylene triphenyl phosphorane (33.8 g) in dry THF (200 ml) was treated with isopropyl isothiocyanate (10.1 g) at 65° C. for 16 h under nitrogen. The mixture was cooled to −78° C. and ethyl bromo-pyruvate (19.5 g) was added. The reaction was allowed to warm slowly to room temperature. After 24 h at room temperature more ethyl bromo-pyruvate (3.17 g) was added and the mixture was stirred at room temperature for 16 h. The reaction was poured into water (1.5 L) and extracted into ether. Drying and evaporation gave an oil which was chromatographed (SiO2/5:1 isohexane-ethyl acetate) to afford the subtitle compound (21.2 g). δ 1HCDCl3 1.23-1.43 (12H, m), 3.46 (1H, m), 4.2-4.35 (4H, m), 6.50 (1H, s), 7.52 (1H, br.d)

Aufarbeitung

  1. temperatureto warm slowly to room temperature
  2. extractionextracted into ether
  3. customDrying
  4. customevaporation
  5. customgave an oil which
  6. customwas chromatographed (SiO2/5:1 isohexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-76c525657b4847d8834fd30940cac0cc
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384950B2

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