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

HRID 2233207

Reaktionsgleichung

Reaktionsgleichung von HRID 2233207
[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 hours stirring, the solvent was evaporated. 1,4-Dioxane was added and evaporated, a few ml of dichloromethane 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 dichloromethane were added
  5. customthe mixture briefly held in an ultrasonic bath
  6. washeluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a2e3fdf223b643c6b417578c9d7a5755
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709483B2

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