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Triethylamine → Tert-butyl 4-[2-(4-(2-phenylethenyl)-3-pyridyl)ethynyl]benzoate

HRID 1006035
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1006035
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]([C:18]1[CH:30]=[CH:29][C:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:20][CH:19]=1)#[CH:17].C(N(CC)CC)C>CN(C=O)C.[Cu](I)(I)I>[C:10]1([CH:9]=[CH:8][C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[C:17]#[C:16][C:18]2[CH:30]=[CH:29][C:21]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])=[CH:20][CH:19]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 13965008Tert-butyl 4-ethynylbenzoateHCID 539315873-Bromo-4-(2-phenylethenyl)pyridine

Produkt 1

HCID 54016878Tert-butyl 4-[2-(4-(2-phenylethenyl)-3-pyridyl)ethynyl]benzoateAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178506583HCID 178506583, VerbindungKatalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

3-Bromo-4-(2-phenylethenyl)pyridine (0.74 g, 2.9 mmol) was dissolved in DMF (1.4 ml). The solution was treated with tert-butyl 4-ethynylbenzoate (0.93 g, 4.6 mmol), copper (III) iodide (0.023 g, 0.21 mmol) and triethylamine (0.64 g, 6.3 mmol). The reaction mixture was degassed by bubbling through argon and the catalyst, bistriphenyl phosphinepalladium dichloride (0.03 g, 0.043 mmol), was added. The reaction was heated to 90-100° C. for 3 hours and then partitioned between ethyl acetate and water. The organic layer was washed with water (3×), dried (MgSO4) and evaporated. The residue was purified by chromatography (eluting with ethylacetate/hexane) to give tert-butyl 4-[2-(4-(2-phenylethenyl)-3-pyridyl)ethynyl]benzoate as a dark oil (0.36 g, 33%).

Aufarbeitung

  1. customThe reaction mixture was degassed
  2. customby bubbling through argon
  3. additionthe catalyst, bistriphenyl phosphinepalladium dichloride (0.03 g, 0.043 mmol), was added
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed with water (3×)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by chromatography (eluting with ethylacetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7243a44edaff415ab5ed24af00dea905
Quelldatensatz
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06787562B2

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