Pyridine → Methyl 5-((hydroxyimino)methyl)thiophene-2-carboxylate

HRID 1397238

Reaktionsgleichung

Reaktionsgleichung von HRID 1397238
Cl.[NH2:2][OH:3].N1C=CC=CC=1.[CH:10]([C:12]1[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:13]=1)=O>CCO>[OH:3][N:2]=[CH:10][C:12]1[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 818924Methyl 5-formylthiophene-2-carboxylate

Produkt 1

HCID 72740488Methyl 5-((hydroxyimino)methyl)thiophene-2-carboxylateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Hydroxylamine hydrochloride (420 mg, 6.1 mmol) and pyridine (0.5 mL) were added to a solution of methyl 5-formylthiophene-2-carboxylate (690 mg, 4.1 mmol) in EtOH (25 mL). The reaction mixture was refluxed for 3 h, cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in diethyl ether, the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to get product methyl 5-((hydroxyimino)methyl)thiophene-2-carboxylate (440 mg, yield 60%), which was carried through without any further purification. 1H NMR (400 MHz, DMSO-d6) δ 12.5 (s, 1H), 7.98 (s, 1H), 7.78 (d, J=4.1 Hz, 1H), 7.51 (d, J=4.1 Hz, 1H), 3.82 (s, 3H). MS (ESI) m/z: Calculated for C7H7NO3S: 185.01. found: 186.0 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-431d63bfd1244dc285cf1cc976b2662e
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901156B2

Verknüpfte Notizen

Wird geladen…