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Water → 2-Ethoxy-4-(4-(4-hydroxyphenyl)-2-methylbut-1-enyl)phenol

HRID 718544
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HRID 718544 반응식
C([Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([CH3:36])=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][Si](C(C)(C)C)(C)C)=[C:21]([O:33][CH2:34][CH3:35])[CH:20]=2)=[CH:11][CH:10]=1)(C)C)(C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[CH2:34]([O:33][C:21]1[CH:20]=[C:19]([CH:18]=[C:17]([CH3:36])[CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[CH:24]=[CH:23][C:22]=1[OH:25])[CH3:35]
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참가 물질

5

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HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86702783Tert-butyl(4-(4-(4-((tert-butyldimethylsilyl)oxy)-3-ethoxyphenyl)-3-methylbut-3-en-1-yl)phenoxy)dimethylsilane

생성물 1

HCID 679822892-Ethoxy-4-(4-(4-hydroxyphenyl)-2-methylbut-1-enyl)phenol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

tert-Butyl(4-(4-(4-((tert-butyldimethylsilyl)oxy)-3-ethoxyphenyl)-3-methylbut-3-en-1-yl)phenoxy)dimethylsilane was dissolved in THF (30 mL), n-Bu4NF (30 mL, 30.0 mmol, 0.7 equiv., 1.0 M in THF) was added, and the mixture was stirred at 25° C. for 1 h. After addition of H2O, the aqueous layer was extracted with MTBE (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 9:1→4:1) to yield 5.87 g (48% over 2 steps) of the title compound as a light yellow oil.

후처리

  1. extractionthe aqueous layer was extracted with MTBE (2×)
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 9:1→4:1)

출처 및 근거

ORD 기록
ord-13af4e3945874477aa2e9f77ea1930f5
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09193935B2

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