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Tetrabutylammonium Fluoride → Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate

HRID 1049408
ノート
印刷プレビュー

反応式

HRID 1049408 の反応式
[Si]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:26]([CH:33]2[CH2:35][CH2:34]2)[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:23]=[CH:24][CH:25]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.[Cl-].[Na+].O>[CH:33]1([CH:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][OH:18])[CH:21]=2)[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:34][CH2:35]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 131736011Ethyl 3-(3-(((tert-butyldiphenylsilyl)oxy)methyl)phenyl)-3-cyclopropylpropanoate

生成物 1

HCID 117759876Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate収率 83.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water
溶媒

実験手順

To a solution of ethyl 3-(3-(((tert-butyldiphenylsilyl)oxy)methyl)phenyl)-3-cyclopropylpropanoate (4.54 g) in THF (20 mL) was added a 1.0 M solution of tetrabutylammonium fluoride in THF (18.7 mL), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added brine, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.94 g) as a colorless oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-c1b4e4c8ab7140f89f8b5484068abecc
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09382188B2

反応ノート

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