Réaction #2080

ord-6642d755fcb048beb2e3a7e3e3b838c6

Équation de réaction

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

Réactifs

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

Réactifs

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

Solvants

O
water
C1CCOC1
THF

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONis added
  2. 2
    Températurethe mixture is heated for a few hours
  3. 3
    TempératureAfter cooling
  4. 4
    Extractionextracted with ethyl acetate
  5. 5
    LavageThe organic phase is then washed with water
  6. 6
    Autredried
  7. 7
    Filtrationfiltered
  8. 8
    Autreevaporated to dryness

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05728688uspto-grants-1998_03