Methanol → Ethyl 6-(4-fluoro-1-naphthyl)-5-hydroxy-6-oxohexanoate

HRID 395663

Reaktionsgleichung

Reaktionsgleichung von HRID 395663
Br[CH:2]([C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([F:23])=[CH:15][CH:14]=1)=[O:12])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C([O-])=[O:25].[Na+].CO>C(OCC)(=O)C>[F:23][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([C:11](=[O:12])[CH:2]([OH:25])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 2723810Sodium FormateHCID 18174722Ethyl 5-bromo-6-(4-fluoro-1-naphthyl)-6-oxohexanoate

Produkt 1

HCID 18174704Ethyl 6-(4-fluoro-1-naphthyl)-5-hydroxy-6-oxohexanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of ethyl 5-bromo-6-(4-fluoro-1-naphthyl)-6-oxohexanoate (34.3 g), sodium formate (34.0 g) and methanol (150 ml) was stirred with heating under reflux for 16 hours. The reaction mixture was diluted with ethyl acetate (500 ml) and washed with water (200 ml×2). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 6-(4-fluoro-1-naphthyl)-5-hydroxy-6-oxohexanoate was obtained as a yellow oil (19.0 g, 65%) from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 16 hours
  3. washwashed with water (200 ml×2)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-efb4936ba28c428d8cd2e3ca784b8740
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605629B1

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