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Dichloromethane → Ethyl 1-(2-acetoxyethyl)-4-bromopyrrole-2-glyoxalate

HRID 638308
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 638308
[Br:1]Br.[C:3]([O:6][CH2:7][CH2:8][N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:5])[CH3:4].ClCCl>CCCCCC.C(OCC)(=O)C>[C:3]([O:6][CH2:7][CH2:8][N:9]1[CH:13]=[C:12]([Br:1])[CH:11]=[C:10]1[C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:5])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 24408BromineHCID 12795013Ethyl 1-(2-acetoxyethyl)pyrrole-2-glyoxalate

Produkt 1

HCID 12795028Ethyl 1-(2-acetoxyethyl)-4-bromopyrrole-2-glyoxalateAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

Three ml. (58.3 mmole) of bromine is added in a dropwise manner to a stirred solution of 14.77 g. (58.3 mmole) of ethyl 1-(2-acetoxyethyl)pyrrole- 2-glyoxalate in 200 ml. anhydrous dichloromethane and cooled to -75° C. After the addition, the reaction is left at -75° C. for 2.5 hours and then the temperature is allowed to increase to room tempearture. The solvent is removed in vacuo, dichloromethane is added to the residue and the solution is washed successively with water, 10% sodium bicarbonate solution and water. The organic phase is dried over sodium sulfate, and the solvent is removed in vacuo. The crude product thus obtained (18.3 g) is subjected to column chromatography on Florisil (1 Kg) using hexane-ethyl acetate (9:1) as the eluting solvent. There is thus obtained upon removal of the solvent, 10.9 g (56%) of ethyl 1-(2-acetoxyethyl)-4-bromopyrrole-2-glyoxalate as an oil having the following physical constants:

Aufarbeitung

  1. additionAfter the addition
  2. temperatureto increase to room tempearture
  3. customThe solvent is removed in vacuo, dichloromethane
  4. additionis added to the residue
  5. washthe solution is washed successively with water, 10% sodium bicarbonate solution and water
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. customthe solvent is removed in vacuo
  8. customThe crude product thus obtained (18.3 g)

Quellen und Nachweise

ORD-Eintrag
ord-acc69b6f86bc49ec8104f1d98903cd17
Quelldatensatz
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04560699

Notizen zur Reaktion

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