Dimethylformamide → ethyl 4-chloro-3-formyl-5-methyl-1H-pyrrole-2-carboxylate

HRID 1948346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948346
O=P(Cl)(Cl)Cl.CN([CH:9]=[O:10])C.[Cl:11][C:12]1[CH:13]=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:15][C:16]=1[CH3:17].C([O-])(=O)C.[Na+]>ClCCCl.O>[Cl:11][C:12]1[C:13]([CH:9]=[O:10])=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:15][C:16]=1[CH3:17]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 66707189ethyl 4-chloro-5-methyl-1H-pyrrole-2-carboxylate

Produkt 1

HCID 86643343ethyl 4-chloro-3-formyl-5-methyl-1H-pyrrole-2-carboxylateAusbeute 30,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

POCl3 in 1,2-dichloroethane (14 mL) was slowly added to a solution of DMF (4.37 mL, 59.79 mmol) in 1,2-dichloroethane (10 mL). The reaction mixture was stirred for 15 min and then Intermediate 7 (2.04 g, 10.87 mmol) was added. The reaction mixture was heated at reflux for 3 h and then cooled to room temperature. The reaction mixture was treated with sodium acetate (10 g) in water (25 mL) and stirred for 1 h. The mixture was extracted with methylene chloride, washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 2:1 hexanes/ethyl acetate) gave the desired compound (720 mg).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. stirringstirred for 1 h
  4. extractionThe mixture was extracted with methylene chloride
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash column chromatography (silica, 2:1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-241e38d15191409aaa061f430f68e776
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399489B2

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