Potassium Iodide → ethyl (RS)-4-(2-acetyl-5-benzyloxy-phenoxy)-4-phenylbutanoate

HRID 322879

Reaktionsgleichung

Reaktionsgleichung von HRID 322879
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]=1[OH:18])=[O:3].Cl[CH:20]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]=1[O:18][CH:20]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:3])[CH3:1]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 3092574'-Benzyloxy-2'-hydroxyacetophenoneHCID 12847348Ethyl 4-chloro-4-phenylbutanoate

Produkt 1

HCID 23204307ethyl (RS)-4-(2-acetyl-5-benzyloxy-phenoxy)-4-phenylbutanoateAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-benzyloxy-2-hydroxyaceto-phenone (1.2 g), ethyl (RS)-4-chloro-4-phenyl-butanoate (1.21 g), potassium carbonate (760 mg), potassium iodide (35 mg) and dimethylformamide (30 mL) is stirred at 100° C. for 8 hours. It is evaporated to dryness and the resulting 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 15-30% ethyl acetate/hexane, affords ethyl (RS)-4-(2-acetyl-5-benzyloxy-phenoxy)-4-phenylbutanoate (0.73 g), in the form of a yellow oil.

Aufarbeitung

  1. customIt is evaporated to dryness
  2. customthe resulting residue is partitioned between ethyl acetate (200 mL) and water (200 mL)
  3. dry with materialThe organic layer is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washFlash chromatography of the resulting oil, eluting with 15-30% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-38a7180b845244e4becca23853d94f6e
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211234B1

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