Dimethylformamide → Methyl pyrrole-2-carboxylate

HRID 34735

Reaktionsgleichung

Reaktionsgleichung von HRID 34735
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].[CH3:9]N(C=O)C.C(N(C(C)C)C(C)C)C.CI>O.C(OCC)(=O)C>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 12473Pyrrole-2-Carboxylic AcidHCID 81531Diisopropylethylamine

Produkt 1

HCID 136930Methyl pyrrole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To pyrrole-2-carboxylic acid (1.11 g., 0.010 mol) in 5 ml. DMF at 0° was added N-(ethyl)diisopropylamine (1.806 ml., 0.0105 mol) followed by methyl iodide (0.654 ml., 0.0105 mol). The mixture was stirred 18 hours at room temperature, diluted with 10 ml. ethyl acetate and 10 ml. H2O, the pH adjusted to 8.5, and the organic layer separated, washed 1×10 ml. H2O, dried over Na2SO4, and stripped with CHCl3 chase to yield title product as a gummy solid containing 10% DMF, 0.93 g.; 1H-nmr (CDCl3) delta (narrow product peaks only): 3.80 (s, 3H), 6.15 (m, 1H), 6.83 (m, 2H).

Aufarbeitung

  1. additiondiluted with 10 ml
  2. customthe organic layer separated
  3. washwashed 1×10 ml
  4. dry with materialH2O, dried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-572ef2f39fcd48d0b00a5f8adfb2462a
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762921

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