Tetrahydrofuran → 8-Ethyl-6-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman

HRID 51689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51689
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:12][CH3:13])[CH:11]=1)[O:8][C:7]([CH3:15])([CH3:14])[CH2:6][C:5]2([CH3:17])[CH3:16].[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20].C(N(CC)CC)C.O1CCCC1>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>[CH2:12]([C:10]1[CH:11]=[C:2]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])[CH:3]=[C:4]2[C:9]=1[O:8][C:7]([CH3:15])([CH3:14])[CH2:6][C:5]2([CH3:17])[CH3:16])[CH3:13]

Komponenten

9

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 695485316-Bromo-8-ethyl-2,2,4,4-tetramethyl chroman2×

Produkt 1

HCID 695486138-Ethyl-6-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman

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 D and using 6-bromo-8-ethyl-2,2,4,4-tetramethyl chroman (Intermediate 46, 0.5 g, 1.61 mmol), (trimethylsilyl)acetylene (1.57 g, 16.1 mmol), triethyl amine (8 mL), anhydrous tetrahydrofuran (10 mL), copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.075 g, 0.11 mmol), followed by flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent, the title compound was obtained as an oil (0.137 g, 27%).

Quellen und Nachweise

ORD-Eintrag
ord-21c959cdebb142968edc971312669324
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713647B2

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