Reacción #2195516

ord-c35149602ede4a0ca33686c35f7191ca

Ecuación de reacción

C[C@]12C=C[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CCC21OCCO1
17,17-ethylenedioxyandrosta-1.5-dien-3β-ol
C[C@]12C=C[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CCC21OCCO1
17,17-ethylenedioxyandrosta-1,5-dien-3β-ol
CC(=O)OC(C)=O
acetic anhydride
→
CC(=O)O[C@H]1C=C[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC23OCCO3)C1
3β-acetoxy-17,17-ethylenedioxyandrosta-1,5-diene

Reactantes

C[C@]12C=C[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CCC21OCCO1
17,17-ethylenedioxyandrosta-1.5-dien-3β-ol
C[C@]12C=C[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CCC21OCCO1
17,17-ethylenedioxyandrosta-1,5-dien-3β-ol
CC(=O)OC(C)=O
acetic anhydride
—
ice water

Reactivos

Ninguno

Disolventes

c1ccncc1
pyridine

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónthe compound was extracted with ether
  2. 2
    LavadoThe organic layer was washed with ice-water several times
  3. 3
    Secadodried over anhydrous magnesium sulfate
  4. 4
    OtroEvaporation of the solvent in vacuo below 35° C.
  5. 5
    Otrogave 1.0 g of crude solid
  6. 6
    OtroRecrystallization from methanol

Procedimiento

A mixture of crude 17,17-ethylenedioxyandrosta-1.5-dien-3β-ol (4, 1.2 g) in pyridine (10 ml) and acetic anhydride (3 ml) was stirred at room temperature for 16 hours. The reaction mixture was poured into ice-water and the compound was extracted with ether. The organic layer was washed with ice-water several times followed by brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent in vacuo below 35° C. gave 1.0 g of crude solid. Recrystallization from methanol gave 3β-acetoxy-17,17-ethylenedioxyandrosta-1,5-diene (5). Mp. 105-6° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07514420B2uspto-grants-2009_04