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Hydrochloric Acid → HCID 10992528, Verbindung

HRID 2299767
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2299767
[H-].[Na+].[OH:3]/[N:4]=[C:5](\[CH3:11])/[C:6]([O:8]CC)=[O:7].Cl[CH2:13][C:14]1[CH:33]=[CH:32][C:17]([O:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:16][CH:15]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:25][C:24]1[O:23][C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:21][C:20]=1[CH2:19][O:18][C:17]1[CH:32]=[CH:33][C:14]([CH2:13][O:3]/[N:4]=[C:5](\[CH3:11])/[C:6]([OH:8])=[O:7])=[CH:15][CH:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 9614318Ethyl 2-hydroxyiminopropionateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

Produkt 1

HCID 10992528HCID 10992528, Verbindung
Ausbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60% in oil, 127 mg) was added under a nitrogen atmosphere to a solution of ethyl E-2-hydroxyiminopropionate (418 mg) and 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (1.00 g) in N,N-dimethylformamide (10 ml) at room temperature and the mixture was stirred for 1 hour. After adding 1N HCl (5 ml), aqueous sodium bicarbonate was added, and then the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residue was subjected to column chromatography on silica gel to obtain an oil from a fraction eluted with ethyl acetate-hexane (1:3, v/v). This oil was dissolved in tetrahydrofuran (10 ml)-methanol (5 ml), and 1N aqueous solution of sodium hydroxide (5 ml) was added and the mixture was stirred at room temperature for 1 hour. 1N HCl (5.5 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residual crystal was recrystallized from ethyl acetate-isopropylether to obtain E-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]propionic acid (849 mg, yield 70%) as colorless crystals. m.p. 147-148° C.

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto obtain an oil from a fraction
  7. washeluted with ethyl acetate-hexane (1:3
  8. dissolutionThis oil was dissolved in tetrahydrofuran (10 ml)-methanol (5 ml), and 1N aqueous solution of sodium hydroxide (5 ml)
  9. additionwas added
  10. stirringthe mixture was stirred at room temperature for 1 hour
  11. addition1N HCl (5.5 ml) was added to the reaction mixture
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated
  16. customThe residual crystal was recrystallized from ethyl acetate-isopropylether

Quellen und Nachweise

ORD-Eintrag
ord-edd48d2f3d8041e3986cedd7615e5096
Quelldatensatz
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06495581B1

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