Trimethylsilylacetylene → HCID 19379151, Verbindung

HRID 2210585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2210585
I[C:2]1[C:11]([NH:12][C:13](=[O:15])[CH3:14])=[C:10]([Cl:16])[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=1[OH:17].[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>CCN(CC)CC.O1CCOCC1.[Cu]I>[CH3:18][Si:19]([C:22]#[C:23][C:2]1[C:11]([NH:12][C:13](=[O:15])[CH3:14])=[C:10]([Cl:16])[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=1[OH:17])([CH3:21])[CH3:20]

Komponenten

6

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 11036030Methyl 4-acetamido-5-chloro-2-hydroxy-3-iodobenzoate

Produkt 1

HCID 19379151HCID 19379151, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8471TriethylamineLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of methyl 3-iodo-4-acetamido-5-chlorosalicylate (2 g) in distilled Et3N (60 ml) and dioxane (40 ml), trimethylsilylacetylene (1 ml), CuI (23 mg), and PdCl2 (PPh3)2 (152 mg) were added. The reaction mixture was stirred at 40° C. for 1.5 hours, after which time the solvents were removed in vacuo. A sample of the residue was purified by column chromatography for analytical purposes eluting with diethyl ether/hexane mixtures to yield the intermediate methyl 3-trimethylsilylethynyl-4-acetamido-5-chloro-salic ylate.

Aufarbeitung

  1. customafter which time the solvents were removed in vacuo
  2. customA sample of the residue was purified by column chromatography for analytical purposes
  3. washeluting with diethyl ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-80bef94b178c4672ba111c1bdedf94da
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05459161

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