Water → 6,7-Dihydro-5H-pyrano[2,3-c]pyridazine-3-carbaldehyde

HRID 656956

Reaktionsgleichung

Reaktionsgleichung von HRID 656956
[CH:1]([C:3]1[N:8]=[N:7][C:6]2[O:9][CH2:10][CH2:11][CH2:12][C:5]=2[CH:4]=1)=C.O.I([O-])(=O)(=O)=[O:15].[Na+]>O1CCOCC1.[Os](=O)(=O)(=O)=O>[N:7]1[C:6]2[O:9][CH2:10][CH2:11][CH2:12][C:5]=2[CH:4]=[C:3]([CH:1]=[O:15])[N:8]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 23667635Sodium periodateHCID 675268253-ethenyl-6,7-dihydro-5H-pyrano[2,3-c]pyridazine

Produkt 1

HCID 866141516,7-Dihydro-5H-pyrano[2,3-c]pyridazine-3-carbaldehydeAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 3-ethenyl-6,7-dihydro-5H-pyrano[2,3-c]pyridazine (100 mg, 0.617 mmol) in 1,4-dioxane (5.5 ml)/water (1.1 ml) was cooled in ice/water and treated with sodium periodate (306 mg, 1.43 mmol) and a 4% aqueous solution of osmium tetroxide (0.55 ml). The mixture was allowed to warm to rt after an hour, and after a total of 4.75 h stirring, the solvent was evaporated. 1,4-Dioxane was added and evaporated, a few ml of DCM were added and the mixture briefly held in an ultrasonic bath. The whole mixture was applied to a silica column and eluted with ethyl acetate to give the product (55 mg, 54%).

Aufarbeitung

  1. customthe solvent was evaporated
  2. addition1,4-Dioxane was added
  3. customevaporated
  4. additiona few ml of DCM were added
  5. customthe mixture briefly held in an ultrasonic bath
  6. washeluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c5112b2101994f7a87e8d10c7a43c565
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

Verknüpfte Notizen

Wird geladen…