반응 #93689

ord-516606992516484ba946ff4032f48a0b

반응 방정식

c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CC(C)(C)C(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3[C@@H](O)[C@H]3O[C@]32C1
5,6β-epoxy-7β-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androstan-17-one
ClCCl
dichloromethane
ClC(Cl)(Cl)Cl
tetrachloromethane
→
CC(C)(C)C(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3[C@H](Cl)[C@H]3O[C@]32C1
7α-chloro-5,6β-epoxy-15β,16β-methylene-3β-pivaloyloxy-5β-androstan-17-one

반응물

c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CC(C)(C)C(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3[C@@H](O)[C@H]3O[C@]32C1
5,6β-epoxy-7β-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androstan-17-one
ClCCl
dichloromethane
ClC(Cl)(Cl)Cl
tetrachloromethane

시약

없음

용매

c1ccncc1
pyridine

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    세척The reaction solution is washed with water
  2. 2
    건조dried over sodium sulfate
  3. 3
    기타evaporated to dryness under vacuum
  4. 4
    workup.STIRRINGThe residue is stirred up with 310 ml of ethanol
  5. 5
    여과filtered
  6. 6
    세척The filter cake is washed with 175 ml of ethanol
  7. 7
    기타dried under vacuum

실험 절차

A solution of 169 g of 5,6β-epoxy-7β-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androstan-17-one in a mixture of respectively 340 ml of dichloromethane, tetrachloromethane, and pyridine is combined with 200 g of triphenylphosphine and stirred for 2 hours at room temperature. The reaction solution is washed with water, dried over sodium sulfate, and evaporated to dryness under vacuum. The residue is stirred up with 310 ml of ethanol and filtered. The filter cake is washed with 175 ml of ethanol and dried under vacuum, thus obtaining 139.2 g of 7α-chloro-5,6β-epoxy-15β,16β-methylene-3β-pivaloyloxy-5β-androstan-17-one. An analytical sample, recrystallized from acetone-hexane, has a melting point of 228° C. [α]D =-100° (chloroform).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04614616uspto-grants-1986_09