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Acetic Acid → ethyl (6E)-6-[(4-hydroxyphenyl)methoxyimino]-6-phenylhexanoate

HRID 584394
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 584394
[Si]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][O:14][NH2:15])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.O=[C:19]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(O)(=O)C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.CCCCCC.O.C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][O:14]/[N:15]=[C:19](/[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)\[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:16][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 3681727Ethyl 6-oxo-6-phenylhexanoateHCID 118211174-(Tert-butyldimethylsilyloxy)benzyloxyamine

Produkt 1

HCID 11089565ethyl (6E)-6-[(4-hydroxyphenyl)methoxyimino]-6-phenylhexanoateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702
Ethanol
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

A mixture of 4-(tert-butyldimethylsilyloxy) benzyloxyamine (5.31 g), ethyl 6-oxo-6-phenylhexanoate (6.76 g), acetic acid (3.54 ml), sodium acetate (3.38 g) and ethanol (150 ml) was heated to reflux for 18 hours. The reaction mixture was cooled to room temperature, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was dissolved in tetrahydrofuran (100 ml), tetrabutylammonium fluoride trihydrate (10.0 g) was added and stirred at room temperature for 1 hour. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl E-6-(4-hydroxybenzyloxyimino)-6-phenylhexanoate (5.64 g, yield 77%) as a colorless oil from an ethyl acetate-hexane (2:7, v/v)-eluted fraction.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in tetrahydrofuran (100 ml)
  8. additiontetrabutylammonium fluoride trihydrate (10.0 g) was added
  9. additionWater was added to the reaction mixture
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-196adbed6fb24b3780daf4c8312ae455
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06924300B2

Notizen zur Reaktion

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