2-Pyrrolidone → Ethyl 3-bromo-2-oxo-3-phenylpropanoate

HRID 414712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414712
C1CNC(=O)C1.[Br:7][Br-]Br.[O:10]=[C:11]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13].N1CCCC1=O>O1CCCC1>[Br:7][CH:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11](=[O:10])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

4

Edukt 2

HCID 120252-PyrrolidoneHCID 12292599Ethyl 2-oxo-3-phenylpropanoate

Produkt 1

HCID 11161566Ethyl 3-bromo-2-oxo-3-phenylpropanoateAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

39.3 g (0.08 mole) of pyrrolidone hydrotribromide (PHT) are introduced portionwise at approximately 10° C. into a solution of 13.9 g (0.072 mole) of ethyl 2-oxo-3-phenylpropanoate (described by E. L. Eliel et al. J. Org. Chem. 37, 505, 1972) in 250 ml of tetrahydrofuran (THF) and 6.1 g (0.072 mole) of 2-pyrrolidone. The temperature of the mixture is allowed to return to 20° C. and the mixture is then heated to 50° C. for 1 h. The mixture is cooled and then poured onto ice. The mixture is extracted with ether and the organic phase washed with water, dried with MgSO4, filtered and evaporated. 18 g of oil are obtained, which is used in the crude state for the next stage of the reaction.

Aufarbeitung

  1. customto return to 20° C.
  2. temperatureThe mixture is cooled
  3. additionpoured onto ice
  4. extractionThe mixture is extracted with ether
  5. washthe organic phase washed with water
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c2f1b16225c2407ba22aee3bb78ac1b7
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04794120

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