反応 #92982

ord-b6af3c6a671240c1b9147dbf61ec04fa

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-].[K+]
potassium formate
→
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)CO
above-identified compound
収率 75.2%
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)CO
16β-Ethyl-17β-glycoloyloxy-4-estren-3-one
収率 75.2%

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-].[K+]
potassium formate

試薬

なし

溶媒

CO
methanol

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    workup.DISTILLATIONThe solvent is distilled off under reduced pressure and water
  2. 2
    workup.ADDITIONis added to the residue
  3. 3
    抽出The mixture is extracted with 150 ml of ethyl acetate
  4. 4
    洗浄the ethyl acetate layer is washed with water and saturated aqueous sodium chloride solution
  5. 5
    乾燥dried over anhydrous magnesium sulfate
  6. 6
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  7. 7
    その他the resulting crystalline precipitate is recrystallized from diethyl ether-n-hexane (1:2)

実験手順

A mixture of 5.0 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 5.0 g of potassium formate is refluxed in 100 ml of methanol for 4 hours. The solvent is distilled off under reduced pressure and water is added to the residue. The mixture is extracted with 150 ml of ethyl acetate, and the ethyl acetate layer is 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 resulting crystalline precipitate is recrystallized from diethyl ether-n-hexane (1:2) to give 3.2 g of the above-identified compound as colorless crystals.

出典

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