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

HRID 1049408
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HRID 1049408 반응식
[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
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 57417360Sodium chloride; water
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c1b4e4c8ab7140f89f8b5484068abecc
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09382188B2

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