Реакция #2080

ord-6642d755fcb048beb2e3a7e3e3b838c6

Уравнение реакции

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

Реактанты

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

Реагенты

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

Растворители

O
water
C1CCOC1
THF

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    workup.ADDITIONis added
  2. 2
    Температураthe mixture is heated for a few hours
  3. 3
    ТемператураAfter cooling
  4. 4
    Экстракцияextracted with ethyl acetate
  5. 5
    ПромывкаThe organic phase is then washed with water
  6. 6
    Другоеdried
  7. 7
    Фильтрацияfiltered
  8. 8
    Другоеevaporated to dryness

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05728688uspto-grants-1998_03