Ammonia → Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

HRID 1077179

반응식

HRID 1077179 반응식
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20]C)=[CH:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2].N.[Li]>O.O1CCCC1.C(O)C>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

참가 물질

7

반응물 3

HCID 222AmmoniaHCID 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-olHCID 3028194Lithium

생성물 1

HCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Add 13β-ethyl-3-methoxy-gona-1,3,5(10)-trien-17β-ol (0.5 g.) in 100 ml. of tetrahydrofuran to 150 ml. of liquid ammonia, followed by 0.5 g. of lithium foil, and stir the mixture for 10 minutes. Add ethanol (6 ml.) and tetrahydrofuran (10 ml.) over a period of 20 minutes. After disappearance of the blue color add water, extract the mixture well with ether and evaporate the washed and dried ether extract. Dissolve the crystalline residue in 50 ml. of methanol and reflux for 30 minutes with 30 ml. of 3N HCL. Remove most of the methanol under reduced pressure, and extract the residue with ether. Chromatograph the ether extract on alumina. Use benzene-ether (1:1) to elute 13-β-ethyl-17β-hydroxy-gon-4-en-3-one; m.p. 152°-55° C.

후처리

  1. extractionextract the mixture well with ether
  2. customevaporate the
  3. washwashed
  4. extractiondried ether extract
  5. dissolutionDissolve the crystalline residue in 50 ml
  6. temperatureof methanol and reflux for 30 minutes with 30 ml
  7. customRemove most of the methanol under reduced pressure
  8. extractionextract the residue with ether
  9. extractionChromatograph the ether extract on alumina
  10. washto elute 13-β-ethyl-17β-hydroxy-gon-4-en-3-one

출처 및 근거

ORD 기록
ord-6727c76ff08c4185bcd15a7d11b6cf86
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03959322

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