Aluminum isopropoxide → 3-Methoxyestra-2,5(10)-dien-17-one

HRID 1077237

反応式

HRID 1077237 の反応式
[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].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>C1(=O)CCCCC1.C1(C)C=CC=CC=1>[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:12]1=[O:21]

参加物

5

反応物 2

HCID 11143Aluminum isopropoxideHCID 1019633-Methoxyestra-2,5(10)-dien-17beta-ol

生成物 1

HCID 227914253-Methoxyestra-2,5(10)-dien-17-one収率 88.1%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 7967Cyclohexanone溶媒

実験手順

Dissolve dl-3-methoxyestra-2,5(10)-dien-17β-ol (4 g) in cyclohexanone (40 ml) and toluene (140 ml) and add a solution of aluminum isopropoxide (4 g) in toluene (56 ml). Reflux in an atmosphere of nitrogen for two hours and cool. Add water (7.5 ml), shake, and then dry by adding sodium sulfate (10 g). Filter and evaporate under vacuum and recrystallize the residue from methanol to obtain dl-3-methoxyestra-2,5(10)-dien-17-one (3.5 g); m.p. 116°-118°; infrared absorption maxima at 5.76 μ, 5.9 μ, 6.01 μ.

後処理

  1. temperatureReflux in an atmosphere of nitrogen for two hours
  2. temperaturecool
  3. dry with materialAdd water (7.5 ml), shake, and then dry
  4. additionby adding sodium sulfate (10 g)
  5. filtrationFilter
  6. customevaporate under vacuum
  7. customrecrystallize the residue from methanol

出典と根拠

ORDレコード
ord-b1399acfce7b47e09acec7d0d8711417
出典データセット
uspto-grants-1976_05
特許番号
US03959322

関連ノート

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