p-Toluenesulfonic acid → 2-[3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-4-yl]acetaldehyde

HRID 1375031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375031
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[CH2:12][CH2:11][O:10][C:9]2[CH:13]=[CH:14][CH:15]=[N:16][C:8]1=2.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[O:10]1[CH2:11][CH2:12][N:7]([CH2:6][CH:2]=[O:1])[C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]1=2

Komponenten

5

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 179639403,4-dihydro-4-[(1,3-dioxolan-2-yl)methyl]-2H-pyrido[3,2-b]-1,4-oxazine

Produkt 1

HCID 179639722-[3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-4-yl]acetaldehydeAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 3,4-dihydro-4-[(1,3-dioxolan-2-yl)methyl]-2H-pyrido[3,2-b]-1,4-oxazine (0.13 g) in acetone (10 ml) and water (1 ml) was heated under reflux in the presence of p-toluenesulfonic acid (2.24 g) for 3 days. The mixture was concentrated in vacuo and the residue was poured into aqueous saturated sodium hydrogen carbonate solution. The water layer was extracted with ethyl acetate three times and the combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel using a mixed solvent of methanol and dichloromethane (1:10) as an eluent. The fractions containing the objective compound were collected and evaporated under reduced pressure to give 2-[3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-4-yl]acetaldehyde (0.09 g) as an oil.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was poured into aqueous saturated sodium hydrogen carbonate solution
  3. extractionThe water layer was extracted with ethyl acetate three times
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel using a mixed solvent of methanol and dichloromethane (1:10) as an eluent
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c8c5958e1c38402fb281b123c9096c6c
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07166598B2

Notizen zur Reaktion

Wird geladen…