تفاعل #78035

ord-456245f79c4a471597f8d42a17d413f7

معادلة التفاعل

C[C@]12CCC(=O)C3OC31CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)C[C@@H]3C[C@]312
17β-hydroxy-4,5-epoxy-14α,15α-methylene-androstan-3-one
Cl
hydrochloric acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
→
C[C@]12CCC(=O)C(Cl)=C1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)C[C@@H]3C[C@]312
4-chloro-17β-hydroxy-14α,15α-methylene-androst-4-ene-3-one

المتفاعلات

C[C@]12CCC(=O)C3OC31CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)C[C@@H]3C[C@]312
17β-hydroxy-4,5-epoxy-14α,15α-methylene-androstan-3-one
Cl
hydrochloric acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate

الكواشف

لا شيء

المذيبات

CC(C)=O
acetone

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىthe acetone is evaporated
  2. 2
    استخلاصThe residue is extracted with dichloromethane
  3. 3
    أخرىThe organic extracts are dried
  4. 4
    تركيزconcentrated
  5. 5
    أخرىAfter crystallization from ethanol

الإجراء التجريبي

17β-hydroxy-4,5-epoxy-14α,15α-methylene-androstan-3-one (1.5 g) is dissolved in 150 mL of acetone and treated at 0° C. with 5.5 mL of concentrated hydrochloric acid. After 24 hours at 0° C., the reaction mixture is neutralized with sodium carbonate solution and the acetone is evaporated. The residue is extracted with dichloromethane. The organic extracts are dried and concentrated. After crystallization from ethanol, 4-chloro-17β-hydroxy-14α,15α-methylene-androst-4-ene-3-one is obtained.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US06710039B1uspto-grants-2004_03