Boron trifluoride etherate → HCID 17932014, Verbindung

HRID 2369220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369220
[CH2:1]([O:8][C:9](=[O:17])[CH2:10][CH2:11][CH:12]([Br:16])[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C(=N)O[C:22]([CH3:25])([CH3:24])[CH3:23].B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C1CCCCC1>[Br:16][CH:12]([CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:17])[C:13]([O:15][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:14]

Komponenten

7

Edukt 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 21197492HCID 21197492, Verbindung2×

Produkt 1

HCID 17932014HCID 17932014, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

5-(Benzyloxy)-2-bromo-5-oxopentanoic acid, 10.0 g (0.033 mole), was dissolved in chloroform, 20 mL. To this was added a solution of t-butyl trichloroacetimidate, 15.9 g (0.073 mole), dissolved in cyclohexane, 50 mL, drop-wise over 30 minutes. The mixture was allowed to stir an additional 5 minutes and boron trifluoride etherate, 100 μL, was added. The reaction mixture was allowed to stir overnight. Sodium bicarbonate, 5 g, was added. After stirring 10 minutes, hexanes, 50 mL, was added and the mixture filtered to remove the solids present. The filtrate was evaporated and the residue purified by flash chromatography, ethyl acetate-hexanes, to give a clear-colorless oil. The yield was 8.2 g, 69% based on starting 5-(Benzyloxy)-2-bromo-5-oxopentanoic acid. NMR is consistent with structure.

Aufarbeitung

  1. stirringto stir overnight
  2. stirringAfter stirring 10 minutes
  3. filtrationthe mixture filtered
  4. customto remove the solids present
  5. customThe filtrate was evaporated
  6. customthe residue purified by flash chromatography, ethyl acetate-hexanes
  7. customto give a clear-colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-f08779cd864644bea82ac0a211c2d606
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703937B2

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