Triethylamine → 6-Bromo-8-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman

HRID 2377333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377333
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](O)[CH:11]=1)[O:8][C:7]([CH3:14])([CH3:13])[CH2:6][C:5]2([CH3:16])[CH3:15].C(N(CC)CC)C.[CH3:24][Si:25]([C:28]#[CH:29])([CH3:27])[CH3:26].C(OCC)(=O)C>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>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24])[CH:11]=1)[O:8][C:7]([CH3:14])([CH3:13])[CH2:6][C:5]2([CH3:16])[CH3:15]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 574242146-Bromo-8-hydroxy-2,2,4,4-tetramethyl chroman2×

Produkt 1

HCID 574242166-Bromo-8-trimethylsilanylethynyl-2,2,4,4-tetramethyl chromanAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8058HexaneLösungsmittel

Versuchsvorschrift

Following General Procedure D and using 6-bromo-8-hydroxy-2,2,4,4-tetramethyl chroman (Intermediate 17, 1.0 g, 3.51 mmol), triethyl amine (5 mL), copper(I)iodide (0.066 g, 0.351 mmol), trimethylsilyl acetylene (2.5 mL, 17.6 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.246 g, 0.351 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 0.5% ethyl acetate in hexane as the eluent, the title compound (1.08 g, ˜100%) was obtained as a brown oil.

Quellen und Nachweise

ORD-Eintrag
ord-a721d3d2852b4ac4bc88c2b375997799
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468391B2

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