Potassium Iodide → ethyl (RS)-4-(3-benzyloxyphenoxy)-4-phenylbutanoate

HRID 322876

Reaktionsgleichung

Reaktionsgleichung von HRID 322876
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][CH:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 138048Benzyl 3-hydroxyphenyl etherHCID 12847348Ethyl 4-chloro-4-phenylbutanoate

Produkt 1

HCID 23204045ethyl (RS)-4-(3-benzyloxyphenoxy)-4-phenylbutanoateAusbeute 17,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 3-benzyloxyphenol (3 g), ethyl (RS)-4-chloro-4-phenylbutanoate (4.53 g), potassium carbonate (4.14 g), potassium iodide (100 mg) and methyl ethyl ketone (100 mL) is heated at reflux for 40 hours. The mixture is evaporated to dryness and the residue is partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer is dried over magnesium sulphate, filtered, and concentrated in vacuo. Flash chromatography of the resulting oil, eluting with a mixture of ethyl acetate and cyclohexane (1:19 v/v), gives ethyl (RS)-4-(3-benzyloxyphenoxy)-4-phenylbutanoate (1 g), in the form of a yellow oil.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 40 hours
  3. customThe mixture is evaporated to dryness
  4. customthe residue is partitioned between ethyl acetate (200 mL) and water (200 mL)
  5. dry with materialThe organic layer is dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washFlash chromatography of the resulting oil, eluting with a mixture of ethyl acetate and cyclohexane (1:19 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-3ba37cce7b7d4a3497a10cae57bd6450
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211234B1

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