Reacción #2383817

Ecuación de reacción

EtOAc

product

5,6,7,8-tetrahydro-5-(4-pentyl)-3H-[1,2,4]oxadiazolo[4,3-a]pyridin-3-one

→

title compound

5,6,7,8-tetrahydro-3-oxo-3H-[1,2,4]oxadiazolo[4,3-a]pyridine-5-butanal

Disolventes

dioxane

H2O

n-butanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas consumed
2. 2
   OtroA precipitate had formed
3. 3
   Filtraciónwas filtered
4. 4
   LavadoThis solid was washed with dioxane
5. 5
   ConcentraciónThe filtrate was concentrated
6. 6
   Otrothe residue was partitioned between H2O/CH2Cl2
7. 7
   SecadoThe organic layer was dried over MgSO4
8. 8
   Concentraciónconcentrated

Procedimiento

The product of Example 27 (0.42 g; 2 mmol) and NaIO4 (0.86 g; 4 mmol) were dissolved in a mixture of 12 mL of dioxane and 8 mL of H2O. Two drops of a 2% solution of OsO4 in n-butanol was added to the mixture. The reaction mixture was stirred until tlc (100% EtOAc) indicated that the starting material was consumed. A precipitate had formed and was filtered. This solid was washed with dioxane. The filtrate was concentrated and the residue was partitioned between H2O/CH2Cl2. The organic layer was dried over MgSO4 and concentrated to afford the title compound as an oil. 1H NMR (CDCl3) d 1.4-2.2 (m, 7H); 2.3-2.7 (m, 4H); 3.7-3.9 (m, 2H); 9.7 (s, 1H).

Fuente