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Boron trifluoride etherate → HCID 15125097, Verbindung

HRID 373374
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 373374
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:14][CH:13]=1.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]([C:4]2[C:5]([CH3:9])=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=2[OH:10])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:16][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 10335PseudocumenolHCID 145139637-(4-Fluorophenyl)-7-hydroxyheptanoic acid

Produkt 1

HCID 15125097HCID 15125097, VerbindungAusbeute 85.488,297 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 2,4,5-trimethylphenol (2.0 mg) and 7-(4-fluorophenyl)-7-hydroxyheptanoic acid (3.5 g) in toluene (60 ml) was added boron trifluoride ethyl ether (0.56 ml) at 70° C. and the reaction was carried out at the same temperature for 6 hours. After cooling in air, the reaction mixture was extracted by addition of water and ethyl acetate. The organic layer was washed in turn with water and saturated saline and dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate/hexane (1 : 5) and the objective compound was recrystallized from ethyl acetate/hexane to obtain 7-(4-fluorophenyl)-7-(2-hydroxy-3,5,6-trimethylphenyl)heptanoic acid (4.5 g) (Compound 1). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Aufarbeitung

  1. temperatureAfter cooling in air
  2. extractionthe reaction mixture was extracted by addition of water and ethyl acetate
  3. washThe organic layer was washed in turn with water and saturated saline
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. washeluted with ethyl acetate/hexane (1 : 5)
  7. customthe objective compound was recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-ca472d532eb147b19b020a2e3e2a476e
Quelldatensatz
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05162571

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