Triethylamine → 3-[4-(5-tert-Butyl-2-methyl-phenylethynyl)-phenyl]-acrylic acid ethyl ester

HRID 1765819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1765819
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([C:12]#[CH:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:16][C:17](=[O:27])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=1)[CH3:15].C(N(CC)CC)C.C(OCC)(=O)C>CCCCCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:14]([O:16][C:17](=[O:27])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][C:23]([C:13]#[C:12][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[CH:9][C:8]=2[CH3:11])=[CH:22][CH:21]=1)[CH3:15]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 211071904-tert-Butyl-2-ethynyl-1-methyl-benzene2×HCID 541932622-Propenoic acid, 3-(4-iodophenyl)-, ethyl ester

Produkt 1

HCID 690739133-[4-(5-tert-Butyl-2-methyl-phenylethynyl)-phenyl]-acrylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8058HexaneLösungsmittel

Versuchsvorschrift

Following General Procedure B and using 4-tert-butyl-2-ethynyl-1-methyl-benzene (Intermediate 110, 0.08 g, 0.47 mmol), ethyl-4-iodocinnamate (0.12 g, 0.4 mmol), triethyl amine (8 mL), copper(I)iodide (0.019 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.07 g, 0.1 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 2–4% ethyl acetate in hexane as the eluent, the title compound was obtained (0.09 g, 55%).

Quellen und Nachweise

ORD-Eintrag
ord-841033041e3c44ba8bbac84a1af734b9
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226951B2

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