Acetic Acid → ethyl (8E)-8-[(4-hydroxyphenyl)methoxyimino]-8-phenyloctanoate

HRID 1070076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070076
[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:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].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:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)\[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:16][CH:17]=1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 10934282Ethyl 8-oxo-8-phenyloctanoateHCID 118211174-(Tert-butyldimethylsilyloxy)benzyloxyamine

Produkt 1

HCID 22344573ethyl (8E)-8-[(4-hydroxyphenyl)methoxyimino]-8-phenyloctanoateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

A mixture of 4-(tert-butyldimethylsilyloxy)benzyloxyamine (3.10 g), ethyl 8-oxo-8-phenyloctanoate (6.32 g), acetic acid (2.07 ml), sodium acetate (1.98 g) and ethanol (80 ml) was heated under reflux for 20 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 (60 ml), tetrabutylammonium fluoride trihydrate (3.98 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-8-(4-hydroxybenzyloxyimino)-8-phenyloctanoate (3.55 g, yield 77%) as a colorless oil from an ethyl acetate-hexane (2:7, v/v)-eluted fraction.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 20 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 (60 ml)
  8. additiontetrabutylammonium fluoride trihydrate (3.98 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-67085f1dc1d04d699cf8a76cf13a89ec
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251926B1

Notizen zur Reaktion

Wird geladen…