Hydrochloric Acid → HCID 68887805, Verbindung

HRID 1760581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1760581
[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:8]([F:15])=[CH:7][C:6]=1I.[C:18]([Si:22]([CH3:29])([CH3:28])[O:23][CH:24]([CH3:27])[C:25]#[CH:26])([CH3:21])([CH3:20])[CH3:19].O=O.Cl>C(N(CC)CC)C.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.[Cu]I>[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:8]([F:15])=[CH:7][C:6]=1[C:26]#[C:25][CH:24]([O:23][Si:22]([C:18]([CH3:19])([CH3:21])[CH3:20])([CH3:29])[CH3:28])[CH3:27]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 977OxygenHCID 110305002-tert-Butyldimethylsiloxybut-3-yneHCID 68890345HCID 68890345, Verbindung

Produkt 1

HCID 68887805HCID 68887805, VerbindungAusbeute 138,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

The title compound (ISP-MS: m/e=361.2 ([M+])) was produced from (4-fluoro-2-iodo-5-trifluoromethyl-phenyl)-carbamic acid methyl ester as follows: (4-Fluoro-2-iodo-5-trifluoromethyl-phenyl)-carbamic acid methyl ester (1520 mg) was dissolved in triethylamine (20 mL). Bis-(triphenylphosphine)-palladium (II) dichloride (193 mg; 5 mol %), copper (I) iodide (52 mg; 5 mol %) and tert-butyl-dimethyl-(1-methyl-prop-2-ynyloxy)-silane (1.22 g; 1.2 equivalent) were added and the reaction mixture was heated 3 h at 50° C. under exclusion of oxygen. The reaction mixture was poured into chilled aqueous hydrochloric acid (25%) and extracted three times with ethyl acetate. The organic phases were pooled, dried over sodium sulfate and the solvent was removed. The residue was chromatographed on silica gel (eluant: hexane/ethyl acetate 95/5). 2.44 g of the {2-[3-(tert-butyl-dimethyl-silanyloxy)-but-1-ynyl]-4-fluoro-5-trifluoromethyl-phenyl}-carbamic acid methyl ester (quantitative yield) was obtained.

Aufarbeitung

  1. additionThe reaction mixture was poured
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed
  5. customThe residue was chromatographed on silica gel (eluant: hexane/ethyl acetate 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-3e55da47160d40ba9068af211eb8ebd9
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06844345B2

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