4-Methoxy cinnamic acid → 1-(2-Iodovinyl)-4-methoxybenzene

HRID 1433938

Reaktionsgleichung

Reaktionsgleichung von HRID 1433938
C([O-])(=O)C.[Li+].[CH3:6][O:7][C:8]1[CH:18]=[CH:17][C:11]([CH:12]=[CH:13]C(O)=O)=[CH:10][CH:9]=1.[I:19]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>O.C(#N)C>[I:19][CH:13]=[CH:12][C:11]1[CH:17]=[CH:18][C:8]([O:7][CH3:6])=[CH:9][CH:10]=1

Komponenten

7

Edukt 4

HCID 132454-Methoxy cinnamic acidHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 3474584Lithium acetate

Produkt 1

HCID 572427761-(2-Iodovinyl)-4-methoxybenzeneAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

By referring to the synthetic method of J. Org. Chem., 1997, 62, 199, to a solution of lithium acetate (280 mg) in water (3 ml) was added acetonitrile (90 ml), the solution was stirred at room temperature, then 4-methoxycinnamic acid (7.5 g), N-iodosuccinimide (10 g) were sequentially added thereto, the solution was stirred for 2 hours at room temperature, and then neutralized with a saturated aqueous solution of sodium bicarbonate. The solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide 1-(2-iodovinyl)-4-methoxybenzene (8.0 g). By referring to the synthetic method of J. Am. Chem. Soc., 1996, 118, 2748, to a solution of 1-(2-iodovinyl)-4-methoxybenzene (7.1 g) and tributyl(4-methoxy-2-nitrophenyl)tin (10 g) in 1-methyl-2-pyrrolidone (100 ml) was added copper(I) thiophene-2-carboxylate (6.6 g) on an ice bath under a nitrogen atmosphere, and the solution was stirred for 25 minutes at room temperature. Tetrahydrofuran was added thereto, the solution was stirred, then filtered through alumina, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (4.7 g).

Aufarbeitung

  1. stirringthe solution was stirred for 2 hours at room temperature
  2. extractionThe solution was extracted with ethyl acetate
  3. washsequentially washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-ab3871690d7d45bd83602221508ca57e
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612114B2

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