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 1765707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1765707
[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, 0.15 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-83454be647f041e7b2678eb1979a5446
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226951B2

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