反応 #93000

ord-a175a5b1bb7a40e594dc1118431ce9c5

反応方程式

CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
O=C(O)c1ccccc1
benzoic acid
[Na+].[OH-]
NaOH
O
water
→
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)COC(=O)c1ccccc1
above-identified compound
収率 89.1%
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)COC(=O)c1ccccc1
16β-Ethyl-17β-benzoyloxyacetoxy-4-estren-3-one
収率 89.1%

反応物

CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
O=C(O)c1ccccc1
benzoic acid
[Na+].[OH-]
NaOH
O
water

試薬

なし

溶媒

CC(C)=O
acetone

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    workup.ADDITIONare added
  2. 2
    温度The mixture is refluxed for 3 hours
  3. 3
    温度After cooling
  4. 4
    workup.DISTILLATIONthe solvent is distilled off under reduced pressure
  5. 5
    抽出the residue is extracted with 100 ml of ethyl acetate
  6. 6
    その他The organic layer is separated
  7. 7
    洗浄washed with water and saturated aqueous sodium chloride solution
  8. 8
    乾燥dried over anhydrous magnesium sulfate
  9. 9
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  10. 10
    その他the residue is chromatographed on a silica gel column
  11. 11
    workup.DISTILLATIONAfter passage of 350 ml of diisopropyl ether, the solvent is distilled off under reduced pressure
  12. 12
    workup.ADDITIONTo the residue is added a small amount of diisopropyl ether
  13. 13
    ろ過followed by filtration

実験手順

In 30 ml of acetone is dissolved 0.49 g of benzoic acid, and 2 ml of 2 N-NaOH and 5 ml of water are added, followed by addition of 0.88 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one. The mixture is refluxed for 3 hours. After cooling, the solvent is distilled off under reduced pressure and the residue is extracted with 100 ml of ethyl acetate. The organic layer is separated, washed with water and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is chromatographed on a silica gel column. After passage of 350 ml of diisopropyl ether, the solvent is distilled off under reduced pressure. To the residue is added a small amount of diisopropyl ether, followed by filtration to give 0.86 g of the above-identified compound as a white powder.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US04609650uspto-grants-1986_09