Reacción #2080

ord-6642d755fcb048beb2e3a7e3e3b838c6

Ecuación de reacción

CC(=O)OCCl
chloromethyl acetate
CC(=O)Cl
acetyl chloride
C=O
formaldehyde
C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
dehydroepiandrosterone
[H-].[Na+]
sodium hydride
[H-].[Na+]
sodium hydride
→
CC(=O)O.C[C@]12CC[C@H](OCO)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
desired compound
CC(=O)O.C[C@]12CC[C@H](OCO)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-hydroxymethoxy-5-androsten-17-one acetate

Reactantes

CC(=O)OCCl
chloromethyl acetate
CC(=O)Cl
acetyl chloride
C=O
formaldehyde
C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
dehydroepiandrosterone
[H-].[Na+]
sodium hydride
[H-].[Na+]
sodium hydride

Reactivos

[Cl-].[Cl-].[Zn+2]
ZnCl2

Disolventes

O
water
C1CCOC1
THF

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONis added
  2. 2
    Temperaturathe mixture is heated for a few hours
  3. 3
    TemperaturaAfter cooling
  4. 4
    Extracciónextracted with ethyl acetate
  5. 5
    LavadoThe organic phase is then washed with water
  6. 6
    Otrodried
  7. 7
    Filtraciónfiltered
  8. 8
    Otroevaporated to dryness

Procedimiento

To a solution of dehydroepiandrosterone (2.88 g, 10 mmol) in THF (100 mL) is added sodium hydride (11 mmol, 60% in oil) at room temperature under an argon atmosphere. When all the sodium hydride has reacted, chloromethyl acetate (prepared from acetyl chloride and formaldehyde (or derivative) using ZnCl2 as catalyst) is added and the mixture is heated for a few hours. After cooling, the mixture is poured into water and extracted with ethyl acetate. The organic phase is then washed with water, dried, filtered and evaporated to dryness to give the desired compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05728688uspto-grants-1998_03