Sodium periodate → 4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde

HRID 475094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475094
[CH3:1][O:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[CH:18]=CC1C=CC=CC=1.I([O-])(=O)(=O)=[O:27].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[CH:18]=[O:27]

Komponenten

6

Edukt 2

HCID 23667635Sodium periodateHCID 866946894-methoxy-5-styryl-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole

Produkt 1

HCID 866946904-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehydeAusbeute 77,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A 1 L three-necked round bottom flask fitted with an overhead stirrer was dried and cooled under a stream of nitrogen then charged with 4-methoxy-5-styryl-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole (25 g, 0.074 mol, 1.0 equiv.) in dioxane (250 mL) and water (80 mL). To this solution was added sodium periodate (36.77 g, 0.17 mol, 2.3 equiv.) and osmium tetroxide (15 mL, 4% aq. soln.) at 0° C., and the reaction mixture was stirred at RT overnight. The reaction mixture was quenched with ice cold water (1 L) and extracted with EtOAc (2×750 mL). The organic layers were combined, washed with brine (500 mL), dried (Na2SO4), filtered and concentrated in vacuo. The crude material was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (40-50% EtOAc) to afford 4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde (15 g, 77%) as a pale yellow solid.

Aufarbeitung

  1. customA 1 L three-necked round bottom flask fitted with an overhead stirrer
  2. customwas dried
  3. temperaturecooled under a stream of nitrogen
  4. customThe reaction mixture was quenched with ice cold water (1 L)
  5. extractionextracted with EtOAc (2×750 mL)
  6. washwashed with brine (500 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified by SiO2 chromatography
  11. washeluting with an EtOAc/hexane gradient (40-50% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-ff448af7d35c42489ab686a9e2864299
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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