Tetrahydrofuran → 3'-Methoxypropiophenone

HRID 1614815

Reaktionsgleichung

Reaktionsgleichung von HRID 1614815
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#N.C1C[O:18]CC1.[Cl-].[NH4+]>C(OCC)C.O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:10](=[O:18])[CH2:1][CH3:2])[CH:12]=[CH:13][CH:14]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 737123-MethoxybenzonitrileHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 5847653'-MethoxypropiophenoneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of ethyl magnesium bromide in diethyl ether (58 ml, 3 M) was added dropwise at room temperature to a mixture of 3-methoxy benzonitrile (21.2 g, 0.159 mol) and dry THF (250 ml). When addition was complete the mixture was stirred for 1 h at room temperature, 3 h at 40° C. and finally stirred overnight at room temperature. Water (250 ml) was added followed by a saturated ammonium chloride solution (250 ml) and the mixture was stirred for 1 h at room temperature. The phases were separated and the aqueous phase was extracted with ethyl acetate (100 ml). The combined organic phases was dried over magnesium sulphate and the solvent evaporated in vacuo to give 25.9 g (99%) of 3'-methoxypropiophenone.

Aufarbeitung

  1. additionWhen addition
  2. stirringthe mixture was stirred for 1 h at room temperature
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (100 ml)
  5. dry with materialThe combined organic phases was dried over magnesium sulphate
  6. customthe solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bcd05ed382bb4254a43112aa2e42dbef
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05198451

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