反応 #92998

ord-e7605e3a96a64f4e8089c5273357f85c

反応方程式

CC(C)(C)C(=O)O
pivalic 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)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
→
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)C(C)(C)C
above-identified compound
収率 87.3%
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)C(C)(C)C
16β-Ethyl-17β-pivaloyloxyacetoxy-4-estren-3-one
収率 87.3%

反応物

CC(C)(C)C(=O)O
pivalic 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)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one

試薬

なし

溶媒

CCOC(C)=O
ethyl acetate
CC(C)=O
acetone
CN(C)C=O
DMF

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 6 hours
  3. 3
    温度After cooling
  4. 4
    その他the organic layer is separated
  5. 5
    抽出The aqueous layer is is further extracted with 50 ml of ethyl acetate
  6. 6
    洗浄washed with water and saturated aqueous sodium chloride solution
  7. 7
    乾燥dried over anhydrous magnesium sulfate
  8. 8
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  9. 9
    洗浄the residue is subjected to column chromatography, elution
  10. 10
    その他The eluate is evaporated under reduced pressure
  11. 11
    その他to remove the solvent

実験手順

In 20 ml of acetone is dissolved 0.61 g of pivalic acid, and 3.0 ml of 2N-NaOH and 10 ml of water are added. And then, 1.2 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 30 ml of DMF are added and the mixture is refluxed for 6 hours. After cooling, 150 ml of ethyl acetate is added and the organic layer is separated. The aqueous layer is is further extracted with 50 ml of ethyl acetate. The organic layers are combined, 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 subjected to column chromatography, elution being carried out with 400 ml of diisopropyl ether. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.1 g of the above-identified compound as a colorless viscous oil.

出典

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