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

HRID 1415034

反応式

HRID 1415034 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-af236d2dc2e74c6a90062a74e8f1b137
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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