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Ammonia → 17Alpha-ethyl-3-methoxyestra-1,3,5(10)-trien-17beta-ol

HRID 1077240
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HRID 1077240 반응식
[CH2:1]([C@:3]1([OH:23])[CH2:8][CH2:7][C@H:6]2[C:9]3[CH2:10][CH2:11][C:12]4[CH:13]=[C:14]([O:21][CH3:22])[CH:15]=[CH:16][C:17]=4[C:18]=3[CH2:19][CH2:20][C@:4]12[CH3:5])[CH3:2].[Li].N.[Cl-].[NH4+]>O1CCCC1.NC1C=CC=CC=1.O>[CH3:2][CH2:1][C:3]1([OH:23])[C:4]2([CH3:5])[CH2:20][CH2:19][CH:18]3[C:17]4[CH:16]=[CH:15][C:14]([O:21][CH3:22])=[CH:13][C:12]=4[CH2:11][CH2:10][CH:9]3[CH:6]2[CH2:7][CH2:8]1
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참가 물질

8

반응물 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 6814549517alpha-Ethyl-3-methoxyestra-1,3,5(10),8-tetraen-17-ol

생성물 1

HCID 8658417Alpha-ethyl-3-methoxyestra-1,3,5(10)-trien-17beta-ol수율 66.2%

시약·촉매·용매 3

HCID 962Water
용매
HCID 6115Aniline용매
HCID 8028Tetrahydrofuran용매

실험 절차

Add dl-17α-ethyl-3-methoxyestra-1,3,5(10),8-tetraen-17-ol (3 g) in tetrahydrofuran (50 ml) to lithium (0.8 g) in aniline (8 ml) and liquid ammonia (200 ml). Stir for two hours, decompose by adding ammonium chloride and water, and extract with ether. Wash, dry and evaporate the organic extract, and crystallize from ethyl acetate-hexane to obtain dl-17α-ethyl-3-methoxyestra-1,3,5(10)-trien-17β-ol (2 g), m.p. 133°--135°; ultraviolet absorption maximum at 279 mμ (ε2,120).

후처리

  1. extractionextract with ether
  2. washWash
  3. customdry
  4. customevaporate the organic extract
  5. customcrystallize from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-7412800590ff40b5ab273d6d6729b4da
출처 데이터셋
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US03959322

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