반응 #92982

ord-b6af3c6a671240c1b9147dbf61ec04fa

반응 방정식

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
수율 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
수율 75.2%

반응물

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

시약

없음

용매

CO
methanol

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

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

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04609650uspto-grants-1986_09