تفاعل #445186

ord-4ba1df8e74404b3c902a955e3370d9c3

معادلة التفاعل

Cl
hydrochloric-acid
CC[C@]12C[C@H](Cl)[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1[C@@H](O)CC2=O
11β-chloro-15α-hydroxy-18-methyl-4-estrene-3,17-dione
CC(=O)OC(C)=O
acetic anhydride
→
CC[C@]12C[C@@H](Cl)[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1[C@@H](OC(C)=O)CC2=O
15α-acetoxy-11α-chloro-18-methyl-4-estrene-3,17-dione

المتفاعلات

—
ice water
Cl
hydrochloric-acid
CC[C@]12C[C@H](Cl)[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1[C@@H](O)CC2=O
11β-chloro-15α-hydroxy-18-methyl-4-estrene-3,17-dione
CC(=O)OC(C)=O
acetic anhydride

الكواشف

لا شيء

المذيبات

c1ccncc1
pyridine

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحThe thus-precipitated product is vacuum-filtered
  2. 2
    workup.DISSOLUTIONdissolved in ethyl acetate
  3. 3
    غسيلwashed with water
  4. 4
    أخرىRecrystallization of the crude product from isopropyl ether

الإجراء التجريبي

1.6 g of 11β-chloro-15α-hydroxy-18-methyl-4-estrene-3,17-dione in 5 ml of pyridine is stirred at room temperature under argon with 1.2 ml of acetic anhydride. After 18 hours, the solution is introduced into hydrochloric-acid-containing ice/water. The thus-precipitated product is vacuum-filtered, dissolved in ethyl acetate, and washed with water. Recrystallization of the crude product from isopropyl ether yields 1.0 g of 15α-acetoxy-11α-chloro-18-methyl-4-estrene-3,17-dione, mp 125.0° C.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04464365uspto-grants-1984_08