Triethylamine → (E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid ethyl ester

HRID 1869835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869835
[CH:1]1([C:4]2[C:15]3[O:14][C:11]4([CH2:13][CH2:12]4)[CH2:10][C:9]([CH3:17])(C)[C:8]=3[CH:7]=[C:6]([C:18]#[CH:19])[CH:5]=2)[CH2:3][CH2:2]1.[CH2:20]([O:22][C:23](=[O:34])/[C:24](/[CH3:33])=[CH:25]/[C:26]1[CH:31]=[CH:30][C:29](I)=[CH:28][CH:27]=1)[CH3:21].[CH2:35](N(CC)CC)C>[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>[CH2:20]([O:22][C:23](=[O:34])/[C:24](/[CH3:33])=[CH:25]/[C:26]1[CH:31]=[CH:30][C:29]([C:19]#[C:18][C:6]2[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[C:15]3[O:14][C:11]4([CH2:12][CH2:13]4)[C:10]([CH3:35])=[C:9]([CH3:17])[C:8]=3[CH:7]=2)=[CH:28][CH:27]=1)[CH3:21]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 225689518-Cyclopropyl-6-ethynyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cvclopropane]HCID 57424206(E)-3-(4-Iodo-phenyl)-2-methyl-acrylic acid ethyl ester2×

Produkt 1

HCID 69069630(E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysator

Versuchsvorschrift

Following General Procedure B and using 8-cyclopropyl-6-ethynyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1′-cyclopropane] (0.077 g, 0.3 mmol), (E)-3-(4-iodo-phenyl)-2-methyl-acrylic acid ethyl ester (Reagent 7, 0.106 g, 0.23 mmol), triethyl amine (3 mL), copper(I)iodide (0.029 g, 0.115 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.064 g, 0.09 mmol) followed by flash column chromatography over silica gel (230-400 mesh), the title compound was obtained (0.06 g, 45%).

Quellen und Nachweise

ORD-Eintrag
ord-10ea3cc63d4b4ff3982bb824a6596b34
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638648B2

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