Morpholine → 3-(2-Morpholino-2-oxoethoxy)benzaldehyde

HRID 619188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619188
[C:1]([CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10])([OH:3])=O.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>O1CCOCC1>[N:14]1([C:1]([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH:9]=[O:10])=[O:3])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Komponenten

4

Edukt 2

HCID 8083MorpholineHCID 6018952-(3-Formylphenoxy)acetic acid

Produkt 1

HCID 164955713-(2-Morpholino-2-oxoethoxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3-(Carboxymethoxy)benzaldehyde (1.63 g, 9.05 mmol) was dissolved in p-dioxane (20 ml) and cooled in an ice bath and then N,N'-carbonyldiimidazole (1.9 g) was added in one portion. The reaction mixture was stirred for 30 minutes, then morpholine (0.8 ml) was added and the mixture was warmed to room temperature and stirred until the reaction was complete. The solvent was removed in vacuo, the residue was partitioned between CHCl3 (100 ml) and 2N HCl (75 ml), the layers were separated, and the aqueous layer was extracted with CHCl3 (2×75 ml). The organic layers were combined, dried over MgSO4 and stripped to afford an oil which was combined with the product from a similar experimental run and purified by column chromatography on silica gel eluting with chloroform to afford 2.1 g of 3-[4-morpholinylcarbonylmethoxy]benzaldehyde.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. stirringstirred until the reaction
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between CHCl3 (100 ml) and 2N HCl (75 ml)
  5. customthe layers were separated
  6. extractionthe aqueous layer was extracted with CHCl3 (2×75 ml)
  7. dry with materialdried over MgSO4
  8. customto afford an oil which
  9. custompurified by column chromatography on silica gel eluting with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-f971c819e6ae4a04832f30c69be7bbeb
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958929

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