Sodium Iodide → 2-[3-Carboxypropyloxy]-dibenzofuran

HRID 128512

Reaktionsgleichung

Reaktionsgleichung von HRID 128512
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[CH2:15]([C:17](Br)(CC)[C:18]([O-:20])=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(=O)CC>[C:18]([CH2:17][CH2:15][CH2:16][O:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1)([OH:20])=[O:19]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 665872-DibenzofuranolHCID 21584491Ethylbromobutyrate

Produkt 1

HCID 194336012-[3-Carboxypropyloxy]-dibenzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

2-Hydroxydibenzofuran (0.5 gm, 2.7 mmol), ethylbromobutyrate (0.78 mL, 5.4 mmol), potassium carbonate (1.1 gm, 8.1 mmol), and sodium iodide (10 mg) were combined in 2-butanone (15 mL). The reaction was refluxed until complete, then the reaction filtered and the solvent removed under reduced pressure. The residue was taken up in 6M aqueous KOH/methanol, 1:1. After the hydrolysis was complete the reaction was acidified to pH 3 and the product extracted with ethyl acetate. The residue was purified by column chromatography (silica gel, ethyl acetate/hexanes/acetic acid, 10:30:60:0.5). The yield was 0.52 gm of product. Mass spectrum: DCI/NH3, (m+H)+ @ m/z 271, (m+NH4)+ @ m/z 288, (m+NH4 ·NH3)+ @ m/z 305.

Aufarbeitung

  1. temperatureThe reaction was refluxed until complete, then the reaction
  2. filtrationfiltered
  3. customthe solvent removed under reduced pressure
  4. extractionthe product extracted with ethyl acetate
  5. customThe residue was purified by column chromatography (silica gel, ethyl acetate/hexanes/acetic acid, 10:30:60:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-9f0b58938871469caa0115f86ab6fdaa
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464746

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