Reaktion #1354402

Reaktionsgleichung

product

6,7,8,9-tetrahydro-5-(2-propenyl)-3H,5H-[1,2,4]oxadiazolo[4,3-a]azepin-3-one

sodium periodate

→

title compound

Ausbeute 67.0%

6,7,8,9-tetrahydro-3-oxo-3H,5H-[1,2,4]oxadiazolo[4,3-a]azepine-5-acetaldehyde

Ausbeute 67.0%

Lösungsmittel

dioxane

water

n-BuOH H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeSince the starting material had not completely reacted
2. 2
   FiltrationA white precipitate was filtered off
3. 3
   Sonstigethe filtrate was removed under reduced pressure to the point where no dioxane
4. 4
   workup.ADDITIONAdditional water (75 mL) was then added to the aqueous layer
5. 5
   Waschenthis aqueous mixture was washed with CH2Cl2 (3×75 mL)
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Sonstigeto afford a yellow oil
8. 8
   SonstigeChromatographic (silica gel) purification of this material
9. 9
   Wascheneluting with the 1:1, ethyl acetate

Vorschrift

EX-8) To a solution of the product of Example 6 in dioxane (200 mL) and water (135 mL) was added sodium periodate (15.11 g, 0.071 mol) and osmium tetraoxide (12 drops of a 1 ppm solution of osmium dioxide in n-BuOH/H2O). The reaction was stirred at room temperature and monitor by thin layer chromatography for one day. Since the starting material had not completely reacted, additional osmium tetraoxide (12 drops of 1 ppm solution of osmium dioxide in n-BuOH/H2O) was added. A white precipitate was filtered off and the filtrate was removed under reduced pressure to the point where no dioxane remained. Additional water (75 mL) was then added to the aqueous layer and this aqueous mixture was washed with CH2Cl2 (3×75 mL). The organic layer was combined, dried over magnesium sulfate, and stripped of all solvent under reduced pressure to afford a yellow oil. Chromatographic (silica gel) purification of this material eluting with the 1:1, ethyl acetate:hexane afforded 4.0 g (67%) of the title compound.

Quelle