Sodium Trifluoroacetate → HCID 11745639, Verbindung

HRID 1449621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1449621
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1I.[F:12][C:13]([F:18])([F:17])C([O-])=O.[Na+]>CN1CCCC1=O.O.[Cu]I>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:13]([F:18])([F:17])[F:12]

Komponenten

6

Edukt 2

HCID 517019Sodium TrifluoroacetateHCID 110650591H-Indole, 2-iodo-1-methyl-

Produkt 1

HCID 11745639HCID 11745639, VerbindungAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 1-methyl-2-iodoindole (4.40 g, 17.3 mmole), sodium trifluoroacetate (24.0 g, 176.5 mmole) and copper(I) iodide (17.1 g, 89.8 mmole) in N-methylpyrrolidone is heated at 160° C. for 6 hours, cooled to room temperature, diluted with water and filtered through diatomaceous earth to remove copper salts. The filtrate is extracted with ether. The extracts are combined, washed with water, dried over MgSO4 and concentrated in vacuo to give a residue. The residue is chromatographed using silica gel and 4:1 hexanes:ethyl acetate as eluent to give the title product as a pale yellow oil which crystallized on standing, 119 g (37% yield), mp 28°-32° C., identified by IR, 1HNMR and 19FNMR analyses.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationfiltered through diatomaceous earth
  3. customto remove copper salts
  4. extractionThe filtrate is extracted with ether
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto give a residue
  9. customThe residue is chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-2663fa617e9048648adb15c309d5b1e1
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05599832

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