Estradiol → Estradiol 3-methyl ether

HRID 649743

反応式

HRID 649743 の反応式
[CH3:1][C@@:2]12[C@@H:18]([OH:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[OH-].[Na+].[CH3:23]OS([O-])(=O)=O>C(O)C.O>[CH3:1][C@@:2]12[C@@H:18]([OH:19])[CH2:17][CH2:16][C@H:15]1[C@@H:14]1[CH2:13][CH2:12][C:11]3[CH:10]=[C:9]([O:20][CH3:23])[CH:8]=[CH:7][C:6]=3[C@H:5]1[CH2:4][CH2:3]2

参加物

6

反応物 3

HCID 5757EstradiolHCID 14798Sodium HydroxideHCID 4694097Methyl sulfate(1-)

生成物 1

HCID 246206Estradiol 3-methyl ether

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of estradiol (10.0 g, 36.7 mmol) in ethanol (100 ml) at reflux was added NaOH (100 mmol) in water (10 ml) followed by the dropwise addition of methylsulfate (Me2SO4) (100 mmol). Neutralization with 10% HCl, subsequent concentration of the mixture followed by filtration through silica gel with ethyl ether, afforded 3-methoxyestradiol as white needles. Dissolving metal reduction of 3-methoxyestradiol was carried out via the methods described by Wilds and affording the known dihydroestradiene derivative as a white solid. (See Feiser, L. F., Feiser, M. “Reagents for Organic Synthesis”, John Wiley and Sons, Inc., New York, 1967, pp. v, 583-4, 622-3.)

後処理

  1. concentrationNeutralization with 10% HCl, subsequent concentration of the mixture
  2. filtrationfollowed by filtration through silica gel with ethyl ether

出典と根拠

ORDレコード
ord-d1284641609c41179e0bd55d32fa2f5e
出典データセット
uspto-grants-2001_08
特許番号
US06271220B1

関連ノート

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