반응 #1693455

ord-22132a803c9d4f2ab14d02cccbdcd98f

반응 방정식

CC(=O)OC1=CC[C@H]2[C@H]3CCc4cc(OC(C)=O)cc(OC(C)=O)c4[C@H]3CC[C@]12C
rac.-1,3,17-triacetoxy-8α-estra-1,3,5(10),16-tetraene
CC(=O)OC(C)=O
acetic anhydride
CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Pb+4]
lead tetraacetate
→
CC(=O)Oc1cc2c(c(OC(C)=O)c1)[C@H]1CC[C@]3(C)C(=O)[C@@H](OC(C)=O)C[C@H]3[C@H]1CC2
rac.-1,3,16β-triacetoxy-8α-estra-1,3,5(10)-trien-17-one

반응물

CC(=O)OC1=CC[C@H]2[C@H]3CCc4cc(OC(C)=O)cc(OC(C)=O)c4[C@H]3CC[C@]12C
rac.-1,3,17-triacetoxy-8α-estra-1,3,5(10),16-tetraene
CC(=O)OC(C)=O
acetic anhydride
CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Pb+4]
lead tetraacetate

시약

없음

용매

CC(=O)O
acetic acid

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타The mixture is evaporated in a forced circulation evaporator
  2. 2
    세척washed neutral with saturated sodium chloride solution
  3. 3
    기타By preparative thin-layer chromatography, minor amounts of starting material are separated
  4. 4
    세척After elution with acetone

실험 절차

Two grams of rac.-1,3,17-triacetoxy-8α-estra-1,3,5(10),16-tetraene is agitated in 40 ml. of glacial acetic acid and 2 ml. of acetic anhydride with 5.5 g. of lead tetraacetate for 15 hours at room temperature. The mixture is evaporated in a forced circulation evaporator. The residue is taken up in ethyl acetate and washed neutral with saturated sodium chloride solution. By preparative thin-layer chromatography, minor amounts of starting material are separated. After elution with acetone, the mixture is afteracetylated with acetic anhydride and pyridine. After working up the reaction mixture and recrsytallization from methylene chloride/isopropyl ether, 700 mg. of rac.-1,3,16β-triacetoxy-8α-estra-1,3,5(10)-trien-17-one is obtained.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US03951958uspto-grants-1976_04