Reacción #93697

ord-1b5da12675b84083aa07322770628b90

Ecuación de reacción

C[C@]12CC[C@H]3[C@@H]([C@H](Cl)[C@H]4O[C@]45C[C@@H](O[Si](Cc4ccccc4)(Cc4ccccc4)Cc4ccccc4)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
3β-tribenzylsilyloxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one
CO
methanol
O=S(=O)(O)O
sulfuric acid
→
CC(C)OC(C)C
diisopropyl ether
C[C@]12CC[C@H]3[C@@H]([C@H](Cl)[C@H]4O[C@]45C[C@@H](O)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β-methylene-5β-androstan-17-one

Reactantes

C[C@]12CC[C@H]3[C@@H]([C@H](Cl)[C@H]4O[C@]45C[C@@H](O[Si](Cc4ccccc4)(Cc4ccccc4)Cc4ccccc4)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
3β-tribenzylsilyloxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one
CO
methanol
O=S(=O)(O)O
sulfuric acid

Reactivos

Ninguno

Disolventes

CCOCC
ether
C1CCOC1
tetrahydrofuran

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadowashed with saturated sodium bicarbonate solution and water
  2. 2
    Secadodried over sodium sulfate
  3. 3
    Concentraciónconcentrated under vacuum

Procedimiento

19 g of 3β-tribenzylsilyloxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one is dissolved in 50 ml of tetrahydrofuran and 50 ml of methanol and agitated with 15 ml of 8% sulfuric acid for 2 hours at room temperature. The mixture is thereafter diluted with ether, washed with saturated sodium bicarbonate solution and water, dried over sodium sulfate, and concentrated under vacuum. By trituration of the thus-obtained solid with diisopropyl ether, 8.7 g of 7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β-methylene-5β-androstan-17-one is obtained, mp 172° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04614616uspto-grants-1986_09