Tetrahydrofuran → 8-Cyclopropyl-4,4-dimethyl-6-(trimethylsilanyl)ethynyl-1-tetralone

HRID 1870005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1870005
[CH:1]1([C:4]2[C:13]3[C:12](=[O:14])[CH2:11][CH2:10][C:9]([CH3:16])([CH3:15])[C:8]=3[CH:7]=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.O1CCCC1.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39]>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.C(OCC)(=O)C>[CH:1]1([C:4]2[CH:5]=[C:6]([C:42]#[C:41][Si:38]([CH3:40])([CH3:39])[CH3:37])[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

Komponenten

9

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 86600196Trifluoro-methanesulfonic acid 4-cyclopropyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester2×

Produkt 1

HCID 211072428-Cyclopropyl-4,4-dimethyl-6-(trimethylsilanyl)ethynyl-1-tetralone

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Following General Procedure B and using trifluoro-methanesulfonic acid 4-cyclopropyl-8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl ester (Intermediate 158, 1.09 g, 3 mmol), triethyl amine (5 mL), tetrahydrofuran (5 mL), copper(I)iodide (0.12 g, 0.6 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.42 g, 0.6 mmol) and (trimethylsilyl)acetylene (2.2 mL, 15 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 7% ethyl acetate in hexane as the eluent, the title compound was obtained as an orange oil (1.05 g, quantitative).

Quellen und Nachweise

ORD-Eintrag
ord-bbc08efd669f4474ad1ee0f011b0d085
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638648B2

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