Sodium Bicarbonate → 6,7-Dihydro[1,4]oxathiino[3,2-c]pyridazine-3-carbaldehyde

HRID 15155

Reaktionsgleichung

Reaktionsgleichung von HRID 15155
[CH:1]([C:3]1[N:8]=[N:7][C:6]2[S:9][CH2:10][CH2:11][O:12][C:5]=2[CH:4]=1)=C.I([O-])(=O)(=O)=[O:14].[Na+].C(=O)(O)[O-].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[N:7]1[C:6]2[S:9][CH2:10][CH2:11][O:12][C:5]=2[CH:4]=[C:3]([CH:1]=[O:14])[N:8]=1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 675272733-Ethenyl-6,7-dihydro[1,4]oxathiino[3,2-c]pyridazine

Produkt 1

HCID 866141526,7-Dihydro[1,4]oxathiino[3,2-c]pyridazine-3-carbaldehydeAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of 3-ethenyl-6,7-dihydro[1,4]oxathiino[3,2-c]pyridazine (200 mg, 1.11 mmol) in 1,4-dioxane/water (10 ml/2 ml) was treated with an aqueous solution of osmium tetroxide (4% w/v, 1 ml) and sodium periodate (0.55 g), initially stirred in an ice-bath for 1.5 hours, then allowed to warm to room temperature. After 1.5 hours the mixture was treated with sodium bicarbonate solution, evaporated to dryness and dissolved in 1,4-dioxane and chloroform. Silica gel was added and the mixture was evaporated to dryness, added to a silica column (20 g), and chromatographed, eluting with 0-100% ethyl acetate in hexane, to afford a pale yellow solid (63 mg, 31%).

Aufarbeitung

  1. customevaporated to dryness
  2. dissolutiondissolved in 1,4-dioxane
  3. additionSilica gel was added
  4. customthe mixture was evaporated to dryness
  5. additionadded to a silica column (20 g)
  6. customchromatographed
  7. washeluting with 0-100% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-e1b48a1aa2ce41328b469642173ae43e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732460B2

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