Ethanol → ((R)-1-benzyloxymethyl-3-butenyloxy)acetaldehyde oxime

HRID 217986

Reaktionsgleichung

Reaktionsgleichung von HRID 217986
C(O[CH:4](OCC)[CH2:5][O:6][C@H:7]([CH2:17][CH:18]=[CH2:19])[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C.C(O)C.S(O)(O)(=O)=O.[NH2:31][OH:32].C([O-])(=O)C.[Na+]>C(O)=O.O>[CH2:10]([O:9][CH2:8][C@H:7]([O:6][CH2:5][CH:4]=[N:31][OH:32])[CH2:17][CH:18]=[CH2:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 159255Hydroxylamine, sulfate (1:1)HCID 517045Sodium AcetateHCID 59281174[(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzene

Produkt 1

HCID 86640913((R)-1-benzyloxymethyl-3-butenyloxy)acetaldehyde oximeAusbeute 112,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 284Formic AcidLösungsmittelHCID 962WaterLösungsmittel3×

Versuchsvorschrift

[(R)-2-(2,2-Diethoxyethoxy)-4-pentenyloxymethyl]benzene (20.0 g) was dissolved in formic acid (160 ml) and water (40 ml), and the mixture was stirred at room temperature for 30 minutes. Next, water (161 ml) and ethanol (400 ml) were added, and then hydroxylamine sulfate (6.38 g) and sodium acetate (8.82 g) were added, followed by stirring at room temperature overnight. Water was added to the reaction solution, and the insoluble matter was dissolved. Then, the excess of ethanol was evaporated under reduced pressure. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (13.7 g).

Aufarbeitung

  1. dissolutionthe insoluble matter was dissolved
  2. customThen, the excess of ethanol was evaporated under reduced pressure
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8153b949c99546c7bd78cf01a586fb24
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198269B2

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