Reacción #355087

Ecuación de reacción

9-fluoro-11β ,17,21-trihydroxy-16α-[(2-methyl-oxiranyl)methoxy]pregn-4-ene-3,20-dione

periodic acid

→

9-fluoro-11β ,17,21-trihydroxy-16α-(2-oxopropoxy)pregn-4-ene-3,20-dione

Rendimiento 22.0%

Disolventes

chloroform

water

tetrahydrofuran

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with chloroform
2. 2
   LavadoThe chloroform solution is washed with 10% sodium bicarbonate solution
3. 3
   Otrodried
4. 4
   Otroevaporated in vacuo
5. 5
   Otroto give an oily residue
6. 6
   Otrochromatographed on a 40 g-silica gel column
7. 7
   LavadoElution with chloroform
8. 8
   Otrogives 400 mg of slightly impure product
9. 9
   OtroThe 990 mg is recrystallized twice from acetone-hexane

Procedimiento

A solution of 1.54 g of 9-fluoro-11β ,17,21-trihydroxy-16α-[(2-methyl-oxiranyl)methoxy]pregn-4-ene-3,20-dione, 21-acetate in 50 ml of tetrahydrofuran is stirred for 270 minutes with a solution of 2.6 g of periodic acid in 20 ml of water. The solution is poured into water and extracted with chloroform. The chloroform solution is washed with 10% sodium bicarbonate solution, dried, and evaporated in vacuo to give an oily residue. This is dissolved in chloroform and chromatographed on a 40 g-silica gel column. Elution with chloroform gives 400 mg of slightly impure product followed by 990 mg of TLC homogeneous solid. The 990 mg is recrystallized twice from acetone-hexane to give 328 mg of 9-fluoro-11β ,17,21-trihydroxy-16α-(2-oxopropoxy)pregn-4-ene-3,20-dione, 21-acetate, melting point 203°-208°C.

Fuente