Reacción #828726

ord-f0bad110599e4c40a3014b4f3ec079ff

Ecuación de reacción

C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2C3=CC=C4C[C@](O)(CC(=O)[O-])CC[C@]4(C)[C@H]3CC[C@]12C
acetate
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2C3=CC=C4C[C@](O)(CC(=O)[O-])CC[C@]4(C)[C@H]3CC[C@]12C
3β,25-Dihydroxycholesta-5,7-diene-3-acetate
[Na+].[OH-]
NaOH
→
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
3b,25-dihydroxycholesta-5,7-diene
Rendimiento 112.7%

Reactantes

C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2C3=CC=C4C[C@](O)(CC(=O)[O-])CC[C@]4(C)[C@H]3CC[C@]12C
acetate
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2C3=CC=C4C[C@](O)(CC(=O)[O-])CC[C@]4(C)[C@H]3CC[C@]12C
3β,25-Dihydroxycholesta-5,7-diene-3-acetate
[Na+].[OH-]
NaOH

Reactivos

Ninguno

Disolventes

CCO
ethanol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe solvent was evaporated in vacuo
  2. 2
    Lavadowashed consecutively with 5% HCl, water, and saturated aqueous NaHCO3
  3. 3
    OtroEvaporation of the solvent

Procedimiento

A solution of acetate 9a (75 mg) in ethanol (10 ml) containing 5% aqueous NaOH (1 ml) was set aside for 24 h and then the solvent was evaporated in vacuo. The residue was taken in ethyl acetate (30 ml) and washed consecutively with 5% HCl, water, and saturated aqueous NaHCO3. Evaporation of the solvent gave (20S) 3b,25-dihydroxycholesta-5,7-diene 9b (74 mg) which was used for the next step without purification; λmax 240, 249, 260 and 272 nm; high resolution mass spec. for C27H44O2 calcd.: 400.3341(M+); found: 400.3334(100%), 398.3162(M+ --H2O, 11%), 385.3101(M+ --CH3, 14%), 380.3086, 24%), 367.3013(M+ --CH3 --H2O, 67%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05552392uspto-grants-1996_09