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Water → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-5,7-diene-1alpha,3beta-diol

HRID 1708760
ノート
印刷プレビュー

反応式

HRID 1708760 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:37])[CH2:13][O:12][CH:11]([CH:14]([C@@H:16]2[C@:33]3([CH3:34])[C@H:19]([C:20]4[C@H:30]([CH2:31][CH2:32]3)[C@:28]3([CH3:29])[C:23]([CH2:24][C@@H:25]([OH:36])[C@@H:26]5[O:35][C@@H:27]53)=[CH:22][CH:21]=4)[CH2:18][CH2:17]2)[CH3:15])[O:10][CH2:9]1.O.C(OCC)(=O)C.CCCCCC>O1CCCC1>[CH3:37][C:8]1([CH3:7])[CH2:9][O:10][CH:11]([CH:14]([C@@H:16]2[C@:33]3([CH3:34])[C@H:19]([C:20]4[C@H:30]([CH2:31][CH2:32]3)[C@:28]3([CH3:29])[C:23]([CH2:24][C@@H:25]([OH:36])[CH2:26][C@@H:27]3[OH:35])=[CH:22][CH:21]=4)[CH2:18][CH2:17]2)[CH3:15])[O:12][CH2:13]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydride2 回HCID 2284392220-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-5,7-dien-3beta-ol

生成物 1

HCID 6785294520-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-5,7-diene-1alpha,3beta-diol収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
60 °C

実験手順

To a suspension of 4 mg (0.1 mmole) of lithium aluminum hydride in 4 ml of dry tetrahydrofuran was added a solution of 3.8 mg (0. 00887 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-5,7-dien-3β-ol in 2 ml of dry tetrahydrofuran at a temperature of 60° C. and the mixture was stirred at 60° C. for 30 minutes. To the reaction mixture was added water to decompose the excess lithium aluminum hydride and the tetrahydrofuran was distilled off under reduced pressure at a temperature not exceeding 60° C. To the residue was added cold 1N-hydrochloric acid and the mixture was extracted with chloroform. The extract was washed with aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent:ethyl acetate-hexane=1:5, v/v) to give 3 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregna-5,7-diene-1α,3β-diol (yield: ca. 80%).

後処理

  1. distillationthe tetrahydrofuran was distilled off under reduced pressure at a temperature not
  2. customexceeding 60° C
  3. additionTo the residue was added cold 1N-hydrochloric acid
  4. extractionthe mixture was extracted with chloroform
  5. washThe extract was washed with aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography (eluent

出典と根拠

ORDレコード
ord-872bdcfde5bf43e0abc361e08de94503
出典データセット
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05359055

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート