Boron trifluoride etherate → HCID 54711575, Verbindung

HRID 2293678

Reaktionsgleichung

Reaktionsgleichung von HRID 2293678
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.[C:13]1([CH:23](O)[CH2:24][CH3:25])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.B(F)(F)F.CCOCC>O1CCOCC1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[C:3]=1[CH:23]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH2:24][CH3:25]

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 124533351-(1-Naphthyl)-1-propanolHCID 546829304-Hydroxycoumarin

Produkt 1

HCID 54711575HCID 54711575, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a cloudy solution of 324 mg of 4-hydroxycoumarin and 373 mg of 1-(1-naphthyl)-propan-1-ol of Preparation 22 in 7 mL of dioxane under an argon atmosphere is added 0.85 mL of boron trifluoride etherate. After stirring overnight the resulting yellow solution is concentrated under reduced pressure. The residue is partioned between water and ethyl acetate; the organic phase is washed with brine, dried (magnesium sulfate), and concentrated. The residue is adsorbed onto silica gel and then flashed column chromatographed using 40% to 50% ethyl acetate in hexane to yield 337 mg of the title product as a pale yellow solid. An analytical sample may be prepared by crystallization from ethyl acetate-hexanes.

Aufarbeitung

  1. concentrationis concentrated under reduced pressure
  2. washthe organic phase is washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-2c5a7267544148f3b60aa14a06517759
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05686486

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