1-Bromo-3-chloropropane → 4-[4-(3-Chloro-propoxy)-phenyl]-4-oxo-butyric acid ethyl ester

HRID 2042625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2042625
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)=[O:8])[CH3:2].Br[CH2:18][CH2:19][CH2:20][Cl:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:18][CH2:19][CH2:20][Cl:21])=[CH:13][CH:14]=1)=[O:8])[CH3:2]

Komponenten

5

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 114359904-(4-Hydroxyphenyl)-4-oxo-butyric acid ethyl ester

Produkt 1

HCID 596520284-[4-(3-Chloro-propoxy)-phenyl]-4-oxo-butyric acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a 1 L round bottom flask, 4-(4-hydroxyphenyl)-4-oxo-butyric acid ethyl ester (8.65 g, 39.0 mmol), 1-bromo-3-chloro-propane (6.1 g, 61.0 mmol), and potassium carbonate (9.3 g, 67.1 mmol) in acetonitrile (300 mL) was heated to reflux 14 h. The reaction was cooled and the solvent concentrated under vacuum. The slurry was partitioned between methylene chloride and water, separated and dried over MgSO4. Purification with silica gel chromatography eluting with hexanes/ethyl acetate (3:1) produced 7.9 g (68%). MS m/z 299 (M+H).

Aufarbeitung

  1. temperatureto reflux 14 h
  2. temperatureThe reaction was cooled
  3. concentrationthe solvent concentrated under vacuum
  4. customThe slurry was partitioned between methylene chloride and water
  5. customseparated
  6. dry with materialdried over MgSO4
  7. customPurification with silica gel chromatography
  8. washeluting with hexanes/ethyl acetate (3:1)
  9. customproduced 7.9 g (68%)

Quellen und Nachweise

ORD-Eintrag
ord-a39f329cf64342c7b998e957275e03bc
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586588B2

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