Water → HCID 67244725, Verbindung

HRID 2425532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2425532
[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1/[CH:28]=[CH:29]/[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[Br:36])(=[O:19])[CH3:18].O>C1(C)C=CC=CC=1.FC(F)(F)C(O)=O>[C:17]([O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[C@H:28]1[C@H:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Br:36])[CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:14]1)(=[O:19])[CH3:18]

Komponenten

6

Edukt 3

HCID 962WaterHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 44139027Phenol, 2-[(1E)-2-(2-bromophenyl)ethenyl]-4-chloro-, 1-acetate

Produkt 1

HCID 67244725HCID 67244725, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

N-benzyl-N-methoxymethyl-N-(trimethylsilylmethyl)amine (5.0 g, 21.06 mmol) was added dropwise with a syringe over 30 minutes to a suspension of (E)-2-(2-bromostyryl)-4-chlorophenyl acetate (Example 1; 7.0 g, 19.9 mmol) in toluene (25 ml) containing trifluoroacetic acid (3 drops) while stirring at room temperature. After additional stirring for one hour water (10 ml) was added. The toluene layer was separated. The aqueous layer was extracted with toluene (25 ml). The combined organic layers were dried with Na2SO4 and evaporated under vacuum to give the crude cycloadduct as a clear and colorless oil, 10.76 g (>100%) in quantitative yield.

Aufarbeitung

  1. additionwas added
  2. customThe toluene layer was separated
  3. extractionThe aqueous layer was extracted with toluene (25 ml)
  4. dry with materialThe combined organic layers were dried with Na2SO4
  5. customevaporated under vacuum
  6. customto give the crude cycloadduct as a clear and colorless oil, 10.76 g (>100%) in quantitative yield

Quellen und Nachweise

ORD-Eintrag
ord-e6441431342a4e2ab9d9546a6e317f4d
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07964739B2

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