反応 #93689

ord-516606992516484ba946ff4032f48a0b

反応方程式

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

反応物

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

試薬

なし

溶媒

c1ccncc1
pyridine

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    洗浄The reaction solution is washed with water
  2. 2
    乾燥dried over sodium sulfate
  3. 3
    その他evaporated to dryness under vacuum
  4. 4
    workup.STIRRINGThe residue is stirred up with 310 ml of ethanol
  5. 5
    ろ過filtered
  6. 6
    洗浄The filter cake is washed with 175 ml of ethanol
  7. 7
    その他dried under vacuum

実験手順

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).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US04614616uspto-grants-1986_09