8-Cyclopropyl-4,4-dimethyl-6-ethynyl-1-tetralone → 3-[4-(4-Cyclopropyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acrylic acid ethyl ester

HRID 1870007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1870007
[CH:1]1([C:4]2[CH:5]=[C:6]([C:17]#[CH:18])[CH:7]=[C:8]3[C:13]=2[C:12](=[O:14])[CH2:11][CH2:10][C:9]3([CH3:16])[CH3:15])[CH2:3][CH2:2]1.[CH2:19]([O:21][C:22](=[O:32])/[CH:23]=[CH:24]/[C:25]1[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=1)[CH3:20]>[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.C(N(CC)CC)C>[CH2:19]([O:21][C:22](=[O:32])[CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][C:28]([C:18]#[C:17][C:6]2[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[C:13]3[C:12](=[O:14])[CH2:11][CH2:10][C:9]([CH3:15])([CH3:16])[C:8]=3[CH:7]=2)=[CH:27][CH:26]=1)[CH3:20]

Komponenten

6

Edukt 2

HCID 211072418-Cyclopropyl-4,4-dimethyl-6-ethynyl-1-tetralone2×HCID 21107276(E)-ethyl 3-(4-iodophenyl)acrylate

Produkt 1

HCID 690726533-[4-(4-Cyclopropyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-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 8471TriethylamineLösungsmittel

Versuchsvorschrift

Following General Procedure B and using 8-cyclopropyl-4,4-dimethyl-6-ethynyl-1-tetralone (Intermediate 160, 0.1 g, 0.42 mmol), (E)-3-(4-iodo-phenyl)-acrylic acid ethyl ester (0.13 g, 0.42 mmol), triethyl amine (1 mL), copper(I)iodide (0.02 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.070 g, 0.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh), the title compound was obtained (0.12 g, 69%).

Quellen und Nachweise

ORD-Eintrag
ord-8025b892831b41f0b7d554a498be986a
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638648B2

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