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

HRID 718544
ノート
印刷プレビュー

反応式

HRID 718544 の反応式
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]
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

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-13af4e3945874477aa2e9f77ea1930f5
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09193935B2

反応ノート

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