Tert-Butyl nitrite → Methyl 5-phenylthiophene-3-carboxylate

HRID 590989

Reaktionsgleichung

Reaktionsgleichung von HRID 590989
N(OC(C)(C)C)=O.N[C:9]1[S:10][C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15]>CN(C)C=O.O>[C:18]1([C:11]2[S:10][CH:9]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

5

Edukt 2

HCID 10906Tert-Butyl nitriteHCID 705256Methyl 2-amino-5-phenylthiophene-3-carboxylate

Produkt 1

HCID 819151Methyl 5-phenylthiophene-3-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of tert-butyl nitrite (428 μL, 3.6 mmol) in N,N-dimethylformamide (5 mL) at 60° C. was dropwise added a solution of methyl 2-amino-5-phenylthiophene-3-carboxylate (11a) (420 mg, 1.8 mmol) in N,N-dimethylformamide (2.5 mL). The mixture was stirred at 60° C. for 1 hour, poured in water (15 mL) and extracted with ethyl acetate (2×20 mL). The organic layer was washed with brine (2×10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in toluene (5 mL) and concentrated in vacuo to provide the desired product (11b) (390 mg, 1.8 mmol, 99%) which was used without further purification.

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. washThe organic layer was washed with brine (2×10 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in toluene (5 mL)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c9133882019c4cfa83115013489f40ff
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238026B2

Verknüpfte Notizen

Wird geladen…