Dimethylformamide → Methyl 3-formyl-4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate

HRID 433882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 433882
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH3:11][C:12]1[CH:13]=[C:14]([C:23]([O:25][CH3:26])=[O:24])[N:15]([CH2:18][C@H:19]2[CH2:21][C@@H:20]2[CH3:22])[C:16]=1[CH3:17].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.O>[CH:8]([C:13]1[C:12]([CH3:11])=[C:16]([CH3:17])[N:15]([CH2:18][C@H:19]2[CH2:21][C@@H:20]2[CH3:22])[C:14]=1[C:23]([O:25][CH3:26])=[O:24])=[O:9]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 69367093methyl 4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate

Produkt 1

HCID 12110455Methyl 3-formyl-4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylateAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Phosphorous oxychloride (2.15 g, 14 mmol) was added to a solution of dimethylformamide (1.10 g, 15 mmol) in toluene (2 ml) and the mixture was stirred at room temperature for 30 minutes. To this mixture was added a solution of methyl 4,5-dimethyl-1-[(1S,2S)-2-methylcyclopropylmethyl]pyrrole-2-carboxylate (2.21 g, 10 mmol) in toluene (6 ml) and the mixture was then heated at 80° C. for 10 hours. After this time, the reaction mixture was poured into water and neutralized with saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated and was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated in vacuo. The residue was chromatographed on a column using ethyl acetate/hexane=10/1 as the eluant to afford the title compound (1.95 g, 78.2%) as a pale yellow oil.

Aufarbeitung

  1. temperaturethe mixture was then heated at 80° C. for 10 hours
  2. customThe organic layer was separated
  3. washwas washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a column

Quellen und Nachweise

ORD-Eintrag
ord-2e27a79cd5c34244975ff0931fdf9aec
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06670360B2

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