Dimethyl Sulfoxide → Methyl 1H-pyrrole-1-carboxylate

HRID 1953628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1953628
[K].[NH:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.Cl[C:8]([O:10][CH3:11])=[O:9].CS(C)=O>C1CCCCC1>[C:8]([N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1)([O:10][CH3:11])=[O:9]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 6586Methyl chloroformateHCID 8027PyrroleHCID 5462222Potassium

Produkt 1

HCID 77962Methyl 1H-pyrrole-1-carboxylateAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

Potassium (5.85 g, 0.15 mol) was added to a solution of 10 ml pyrrole (0.145 mol) in 80 ml hot cyclohexane in several portions. The mixture was refluxed for 1 hour. To this cold solution was added 15 g (0.16 mol) methyl chloroformate slowly. After addition, the mixture was stirred at room temperature for 30 minutes. During this period, 2.5 ml dimethyl sulfoxide was added for catalysis. After quenching with ice-water, the organic layer was separated and the aqueous layer extracted with ether. The combined organic layer was washed with 10% sodium bicarbonate, sat. sodium chloride and dried over magnesium sulfate. Removal of solvent yielded 17.4 g of a liquid. Bulb to bulb distillation gives 16.5 g N-carbomethoxy pyrrole 21 as a colorless liquid, yield 91%. The product requires storage at -20° C.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 1 hour
  2. additionAfter addition
  3. waitDuring this period
  4. customAfter quenching with ice-water
  5. customthe organic layer was separated
  6. extractionthe aqueous layer extracted with ether
  7. washThe combined organic layer was washed with 10% sodium bicarbonate, sat. sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customRemoval of solvent

Quellen und Nachweise

ORD-Eintrag
ord-e053318ed2bd4f6e911011e0a8cb5af4
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06117889

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