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Water → 4-[(4-Ethynylphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

HRID 2100129
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2100129
[CH3:1][C:2]1([CH3:30])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[C:10]([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[C:25][Si](C)(C)C)=[CH:20][CH:19]=2)[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:3]1.C([O-])([O-])=O.[K+].[K+].O>CO>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([C:10](=[C:4]2[CH2:3][C:2]([CH3:30])([CH3:1])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5]2)[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:19][CH:20]=1)#[CH:25]
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Komponenten

5

Edukt 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 686547694-((3,3,5,5-Tetramethylcyclohexylidene){4-[(trimethylsilyl)ethynyl]phenyl}methyl)phenol

Produkt 1

HCID 114052154-[(4-Ethynylphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenolAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

4-((3,3,5,5-Tetramethylcyclohexylidene){4-[(trimethylsilyl)ethynyl]phenyl}methyl)phenol (146) (0.175 g, 0.42 mmol) was dissolved in MeOH (10 mL). To this solution was added K2CO3 (0.18 g, 1.26 mmol). The reaction mixture was stirred at room temperature overnight, poured into water (10 mL) and extracted with EtOAc (2×50 mL). The combined organic phase washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as brown solid. The crude product was purified by chromatography on a silica gel column eluted with a gradient from hexanes to 15% EtOAc:hexanes to give 0.14 g (97%) of the title compound 147 as white solid. mp 138-139° C. 1H NMR (400 MHz, CDCl3): δ 0.91 (s, 6H), 0.92 (s, 6H), 1.28 (s, 2H), 1.93 (s, 2H), 1.97 (s, 2H), 3.03 (s, 1H), 4.55 (br s, 1H), 6.73 (d, J=8.5 Hz, 2H), 7.01 (d, J=8.4 Hz, 2H), 7.11 (d, J=8.2 Hz, 2H), 7.39 (d, J=8.2 Hz, 2H). LCMS (ESI): m/z 343 (M−H)−.

Aufarbeitung

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe combined organic phase washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customto give the crude product as brown solid
  7. customThe crude product was purified by chromatography on a silica gel column
  8. washeluted with a gradient from hexanes to 15% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-582a26b608984a75bec3cf6fd7ecfb31
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07569601B2

Notizen zur Reaktion

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