Ammonia → Estradiol 3-methyl ether

HRID 1415033

反応式

HRID 1415033 の反応式
[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

参加物

8

反応物 5

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

生成物 1

HCID 246206Estradiol 3-methyl ether収率 31.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0dbd3bbdec054d73afc21a3c0aac6266
出典データセット
uspto-grants-1977_01
特許番号
US04002746

関連ノート

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