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Diethyl Ether → 1-(4-Methoxyphenyl)-2-phenyl-1-(4-pivaloyloxyphenyl)-3-butene

HRID 1926574
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1926574
[C:1]([O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C[Si](C)(C)[CH2:18][CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O.C(=O)(O)[O-].[Na+].[CH2:35]([O:37][CH2:38][CH3:39])C>C1(OC)C=CC=CC=1.[Cl-].[Hf+4].[Cl-].[Cl-].[Cl-]>[CH3:35][O:37][C:38]1[CH:39]=[CH:10][C:9]([CH:12]([C:11]2[CH:14]=[CH:15][C:8]([O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:9][CH:10]=2)[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH2:18])=[CH:8][CH:15]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 142474CinnamyltrimethylsilaneHCID 146834134-Formylphenyl 2,2-dimethylpropanoateHCID 86585896Sodium bicarbonate water

Produkt 1

HCID 251119881-(4-Methoxyphenyl)-2-phenyl-1-(4-pivaloyloxyphenyl)-3-buteneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9927068
Hafnium chloride (HfCl4) (6CI,8CI); Hafnium chloride; Hafnium tetrachloride; Hafnium(IV) chloride; Hafnium chloride (HfCl4), (T-4)-
Katalysator
HCID 7519AnisoleLösungsmittel2×

Versuchsvorschrift

Under an argon atmosphere, hafnium chloride (39.2 mg, 0.122 mmol) is suspended in anisole (3, 0.02 mL), and under ice cooling, an anisole (0.22 mL) solution of 4-(pivaloyloxy)benzaldehyde (1, 25 mg, 0.121 mmol) and trimethylcinnamylsilane (2, 46.7 mg, 0.245 mmol) was slowly added dropwise. After stirring overnight at room temperature, saturated sodium bicarbonate water (5 mL) was poured into the reaction mixture with vigorous stirring, diethyl ether (10 mL) was added and extraction was performed. Extractions were further carried out two times with diethyl ether (10 mL), the organic layers were combined, washed with a saturated sodium chloride aqueous solution (5 mL), dried with anhydrous magnesium sulfate, and concentrated. The residue was purified by thin layer chromatography (hexane:methylene chloride:diethyl ether=4:1:1), and the subject compound (4, 37.7 mg) was obtained as a colorless oily substance (yield 75%, syn/anti mixture).

Aufarbeitung

  1. additionwas added
  2. extractionextraction
  3. extractionExtractions
  4. washwashed with a saturated sodium chloride aqueous solution (5 mL)
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by thin layer chromatography (hexane:methylene chloride:diethyl ether=4:1:1)
  8. customthe subject compound (4, 37.7 mg) was obtained as a colorless oily substance (yield 75%, syn/anti mixture)

Quellen und Nachweise

ORD-Eintrag
ord-229e7c4452d643f5bf3d904a69ab9b34
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08183235B2

Notizen zur Reaktion

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