Reacción #724800

ord-ef76c2cfb25c45848d5eb8ad055c7b8e

Ecuación de reacción

C[C@@H]1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC(=O)[C@@]1(C)C[C@H]2O
11α-hydroxy-7α-methylestr-4-ene-3,17-dione
O=S(=O)(O)O
sulfuric acid
C
charcoal
CC(=O)O
acetic acid
→
C[C@@H]1CC2=CC(=O)CC[C@@H]2[C@H]2C(=O)C[C@]3(C)C(=O)CC[C@H]3[C@@H]21
7α-Methylestr-4-ene-3,11,17-trione

Reactantes

C[C@@H]1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC(=O)[C@@]1(C)C[C@H]2O
11α-hydroxy-7α-methylestr-4-ene-3,17-dione
O=S(=O)(O)O
sulfuric acid
C
charcoal
CC(=O)O
acetic acid

Reactivos

[Cr+6].[O-2].[O-2].[O-2]
chromium trioxide
[Cr+6].[O-2].[O-2].[O-2]
chromium trioxide
O
water
O.O=S(=O)([O-])[O-].[Mn+2]
manganese sulfate monohydrate

Disolventes

O
water
O
water
CCOC(C)=O.ClCCl
ethyl acetate methylene chloride
O
water

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturacooled to about 10° in a cold water bath
  2. 2
    workup.ADDITIONThe following reagents are added
  3. 3
    Otrothe crystals of the product are collected
  4. 4
    Lavadowashed with water
  5. 5
    Otrodried
  6. 6
    Otroto give a solid
  7. 7
    Filtraciónfiltered through celite
  8. 8
    Concentraciónconcentrated
  9. 9
    Otroto give crystals, UV (ethyl alcohol) λmax =239 nm (ε=16250)

Procedimiento

A mixture of 11α-hydroxy-7α-methylestr-4-ene-3,17-dione (A, obtained from Fermentation) and acetic acid (7.5 ml) is stirred and cooled to about 10° in a cold water bath. The following reagents are added: water (6 drops), manganese sulfate monohydrate (0.1 g) in water (1 ml), chromium trioxide (0.66 g) in water (2 ml), and concentrated sulfuric acid (0.6 ml). The chromium trioxide solution is added over a 15 minute period. After 1/2 hour water (10 ml) is added and the crystals of the product are collected, washed with water and dried to give a solid. The solid is dissolved in hot ethyl acetate/methylene chloride (1/1) and decolorized with a little charcoal and silica gel and then filtered through celite. The appropriate fractions are pooled and concentrated to give crystals, UV (ethyl alcohol) λmax =239 nm (ε=16250); IR (mull) 1740, 1707, 1672 and 1616; MS (m/e)=300, 282, 272, and 258.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04557867uspto-grants-1985_12