Reacción #70374

ord-bc04db4cc0984fdc93040b46a6bd0afc

Ecuación de reacción

C#C[C@H]1C[C@@H]2[C@H](CC[C@@]3(C)[C@H]2CC24OCCOC23OCCO4)[C@@]2(C)CCCCC12
17,17-bis(ethylendioxy)-6α-ethynylandrostane
C=C1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
6-methyleneandrostane-3,17-dione
→
C#C[C@H]1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
title compound
Rendimiento 46.0%
C#C[C@H]1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
6α-Ethynylandrostane-3,17-dione
Rendimiento 46.0%

Reactantes

C#C[C@H]1C[C@@H]2[C@H](CC[C@@]3(C)[C@H]2CC24OCCOC23OCCO4)[C@@]2(C)CCCCC12
17,17-bis(ethylendioxy)-6α-ethynylandrostane
C=C1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
6-methyleneandrostane-3,17-dione

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    LavadoThe combined organic extracts were washed with H2O
  2. 2
    Secadodried over Na2SO4
  3. 3
    Otroevaporated to dryness
  4. 4
    OtroThe residue was purified by flash chromatography (SiO2, cyclohexane/CH2Cl2/acetone 80/10/10)

Procedimiento

The title compound II-am was prepared in 46% yield from 3,3:17,17-bis(ethylendioxy)-6α-ethynylandrostane by the procedure described for the preparation of 6-methyleneandrostane-3,17-dione (II-ac, Prepn. 13). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, cyclohexane/CH2Cl2/acetone 80/10/10). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 2.69-0.78 (22H, m), 1.12 (3H, s), 0.87 (3H, s).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08536160B2uspto-grants-2013_09