Ammonia → Estradiol 3-methyl ether

HRID 1077213

반응식

HRID 1077213 반응식
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[CH2:16][CH2:15][C@@:13]4([CH3:14])[C@@H:9]([CH2:10][CH2:11][C@@H:12]4[OH:21])[C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=1.N.NC1C=CC=CC=1.[Li].[Cl-].[NH4+]>O1CCCC1.O>[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

참가 물질

8

반응물 5

HCID 222AmmoniaHCID 6115AnilineHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 110552063-Methoxyestra-1,3,5(10),8-tetraen-17beta-ol

생성물 1

HCID 246206Estradiol 3-methyl ether수율 31.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Add dl-3-methoxyestra-1,3,5(10),8-tetraen-17β-ol (37.5 g) in tetrahydrofuran (350 ml) to a stirred solution of liquid ammonia (1 liter) and aniline (45 ml). Add lithium (2 g), stir for 30 minutes, and then add ammonium chloride (20 g) followed by water. Extract with ether-benzene (1:1) and wash the organic solution with water, excess 3N hydrochloric acid, water and dry. Evaporate the solvent and recrystallize the residue from ethyl acetate-hexane to obtain dl-3-methoxyestra-1,3,5(10)-trien-17β-ol (12 g), m.p. 121-124°; ultraviolet absorption peak at 278 mμ (ε1,810); infrared maxima at 3.0 μ, 6.2 μ, 6.75 μ.

후처리

  1. extractionExtract with ether-benzene (1:1)
  2. washwash the organic solution with water, excess 3N hydrochloric acid, water
  3. customdry
  4. customEvaporate the solvent
  5. customrecrystallize the residue from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-d4b607b6e1e14a5dbe63e47e523ca206
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03959322

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