Ammonia → 3-Methoxyestra-2,5(10)-dien-17beta-ol

HRID 1077214

반응식

HRID 1077214 반응식
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([OH:21])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.[Li].N.[Cl-].[NH4+]>O1CCCC1.O.C(O)C>[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]1[OH:21]

참가 물질

8

반응물 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 246206Estradiol 3-methyl etherHCID 3028194Lithium

생성물 1

HCID 1019633-Methoxyestra-2,5(10)-dien-17beta-ol수율 64.2%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Add dl-3-methoxyestra-1,3,5(10)-trien-17β-ol (1.3 g) in tetrahydrofuran (40 ml) to a stirred solution of lithium (1.3 g) in liquid ammonia (100 ml). After 15 minutes add ethanol (20 ml) dropwise and when the blue color is discharged add ammonium chloride and water and extract the mixture with ether. Wash, dry and evaporate the ethereal solution and recrystallize the residue from ethanol-hexane to obtain dl-3-methoxyestra-2,5(10)-dien-17β-ol (0.84 g), m.p. 120-123°; infrared absorption maxima at 3.25 μ, 5.8 μ, 6 μ.

후처리

  1. extractionextract the mixture with ether
  2. washWash
  3. customdry
  4. customevaporate the ethereal solution
  5. customrecrystallize the residue from ethanol-hexane

출처 및 근거

ORD 기록
ord-f388ce3e178d4d83ac4255bc30913c7e
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03959322

연결된 노트

불러오는 중…