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Dimethyl (2-propynyloxy)(1,1,2-trimethylpropyl)-silane → (4-Bromo-2-{3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-prop-1-ynyl}-5-methyl-phenyl)-carbamic acid methyl ester

HRID 585861
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 585861
[CH3:1][O:2][C:3](=[O:14])[NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[CH:7][C:6]=1I.[CH3:15][Si:16]([CH3:27])([O:23][CH2:24][C:25]#[CH:26])[C:17]([CH3:22])([CH3:21])[CH:18]([CH3:20])[CH3:19]>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:14])[NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[CH:7][C:6]=1[C:26]#[C:25][CH2:24][O:23][Si:16]([CH3:27])([CH3:15])[C:17]([CH3:22])([CH3:21])[CH:18]([CH3:20])[CH3:19]
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Komponenten

4

Edukt 2

HCID 18455989Dimethyl (2-propynyloxy)(1,1,2-trimethylpropyl)-silaneHCID 57543475Methyl (4-Bromo-2-iodo-5-methylphenyl)carbamate

Produkt 1

HCID 68890098(4-Bromo-2-{3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-prop-1-ynyl}-5-methyl-phenyl)-carbamic acid methyl esterAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 3.70 g (4-bromo-2-iodo-5-methyl-phenyl)-carbamic acid methyl ester and 0.070 g bis-triphenylphosphine palladium dichloride and 0.038 g cuprous iodide in 25 ml triethylamine was added 2.38 g dimethyl (2-propynyloxy)(1,1,2-trimethylpropyl)-silane and the mixture was heated 2 h at reflux. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was washed with 1N hydrochloric acid, sodium bicarbonate and brine, dried with magnesium sulfate and purified by chromatography on silica gel with hexane:ethyl acetate=4:1 to yield 1.92 g (4-bromo-2-{3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-prop-1-ynyl}-5-methyl-phenyl)-carbamic acid methyl ester as a light brown oil. MS: M+NH4+=457.0 M+Na+=462.2

Aufarbeitung

  1. temperaturethe mixture was heated 2 h
  2. temperatureat reflux
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customThe phases were separated
  5. washthe organic phase was washed with 1N hydrochloric acid, sodium bicarbonate and brine
  6. dry with materialdried with magnesium sulfate
  7. custompurified by chromatography on silica gel with hexane

Quellen und Nachweise

ORD-Eintrag
ord-934c0d1132604cada6ebd4c172bbdbde
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06933387B2

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