反応 #2383810

反応方程式

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

収率 67.0%

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

収率 67.0%

溶媒

dioxane

water

n-BuOH H2O

反応条件

後処理

1. 1
   その他Since the starting material had not completely reacted
2. 2
   ろ過A white precipitate was filtered off
3. 3
   その他the 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
   洗浄this aqueous mixture was washed with CH2Cl2 (3×75 mL)
6. 6
   乾燥dried over magnesium sulfate
7. 7
   その他to afford a yellow oil
8. 8
   その他Chromatographic (silica gel) purification of this material
9. 9
   洗浄eluting with the 1:1, ethyl acetate

実験手順

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. 1H NMR (CDCl3, 300 MHz) d 1.2-2.5 (m, 6H), 2.59 (q, 2H), 2.92 (m, 2H), 4.79 (m, 1H), 9.79 (ss, 1H). 13C NMR (CDCl3, 75 MHz) d 24.12, 31.52, 32.00, 45.61, 49.10, 53.98, 159.9, 160.8, 198.1.

出典