Hydrochloric Acid → Ethyl 4-(4-bromophenyl)-3-oxobutanoate

HRID 727245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 727245
C([Mg]Cl)(C)C.[CH2:6]([O:8][C:9](=[O:14])[CH2:10][C:11]([OH:13])=O)[CH3:7].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]C(Cl)=O)=[CH:18][CH:17]=1.Cl>O1CCCC1>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:11](=[O:13])[CH2:10][C:9]([O:8][CH2:6][CH3:7])=[O:14])=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 70615Monoethyl malonateHCID 181552Benzeneacetyl chloride, 4-bromo-HCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 18944022Ethyl 4-(4-bromophenyl)-3-oxobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

1 l (2 mol) of a 2M solution of isopropylmagnesium chloride in tetrahydrofuran is added dropwise to a solution of 125 g (0.95 mol) of malonic acid monoethyl ester in 1 l of tetrahydrofuran at 0° C. and the mixture is stirred at 20° C. for 1 hour. 146 g (0.63 mol) of 4-bromophenylacetyl chloride are then added dropwise at 20° C., and the reaction mixture is stirred at this temperature for 2 hours and brought to pH=3 with 1N hydrochloric acid. It is stirred overnight, the phases are separated, the aqueous phase is washed with diethyl ether, the combined organic phases are washed with water and aqueous sodium bicarbonate solution, the solvent is distilled off, the residue is dissolved in methylene chloride, the solution is dried with sodium sulphate and filtered over silica gel using methylene chloride and the solvent is removed on a rotary evaporator.

Aufarbeitung

  1. stirringthe reaction mixture is stirred at this temperature for 2 hours
  2. stirringIt is stirred overnight
  3. customthe phases are separated
  4. washthe aqueous phase is washed with diethyl ether
  5. washthe combined organic phases are washed with water and aqueous sodium bicarbonate solution
  6. distillationthe solvent is distilled off
  7. dissolutionthe residue is dissolved in methylene chloride
  8. dry with materialthe solution is dried with sodium sulphate
  9. filtrationfiltered over silica gel
  10. customthe solvent is removed on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-de48bb460ed047e9bc35305ef6302048
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05712296

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