Dimethylformamide → Methyl 2-phenylbenzofuran-5-carboxylate

HRID 970798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970798
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:13]1([C:19]#[CH:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN(C)C(=N)N(C)C.CN(C=O)C>[Cu]I.O>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[CH:10][C:11]2[O:12][C:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:20][C:2]=2[CH:3]=1)=[O:6]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 10821PhenylacetyleneHCID 664601,1,3,3-TetramethylguanidineHCID 11346465Methyl 4-hydroxy-3-iodobenzoate

Produkt 1

HCID 66865443Methyl 2-phenylbenzofuran-5-carboxylateAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-iodo-4-hydroxybenzoate 26 (1 g, 3.6 mmol), phenylacetylene (2 ml, 18 mmol), tetramethylguanidine (4.5 ml, 36 mmol), copper(I)iodide (34 mg, 1.8 mmol), bis(triphenylphosphine)palladium (II)chloride (130 mg, 1.8 mmol) and DMF (20 ml) was stirred at room temperature overnight. The reaction mixture was poured into water, extracted, washed and dried. After evaporation of the solvent, the residue was purified by chromatography to give about 0.9 g of 2-phenyl-benzofuran-5-carboxylic acid methyl ester 27.

Aufarbeitung

  1. extractionextracted
  2. washwashed
  3. customdried
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4042b37d30884d6ab7b6a9095288db44
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312230B2

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