Trifluoroacetic acid → HCID 67044183, Verbindung

HRID 1944471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1944471
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[CH3:15][O:16][C:17](=[O:30])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[CH:21]=[C:20]1[CH3:29].[C:31]1([S:37]([C:40]2[CH:47]=[CH:46][CH:45]=[CH:44][C:41]=2[CH:42]=O)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCl.ClCCCl>[CH3:15][O:16][C:17](=[O:30])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[C:21]([CH2:42][C:41]2[CH:44]=[CH:45][CH:46]=[CH:47][C:40]=2[S:37]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:39])=[O:38])=[C:20]1[CH3:29]

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 6409162-(Phenylsulfonyl)benzaldehydeHCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetate

Produkt 1

HCID 67044183HCID 67044183, VerbindungAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A mixture of triethylsilane (0.71 g), trifluoroacetic acid (0.53 g) and 1,2-dichloroethane (2.0 mL) at −10° C. was treated dropwise with a mixture of (5-fluoro-2-methylindol-1-yl)acetic acid methyl ester (0.091 g), 2-benzenesulfonylbenzaldehyde (0.12 g) and 1,2-dichloroethane (3.0 mL), and the resulting mixture was stirred at −10° C. for 15 minutes and then at room temperature for 2 hours. The mixture was diluted with dichloromethane, washed with saturated aqueous sodium hydrogen carbonate solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and dichloromethane (1:1 to 0:1 by volume) to afford the title compound as a colourless gum (0.17 g).

Aufarbeitung

  1. waitat room temperature for 2 hours
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel
  6. washeluting with a mixture of cyclohexane and dichloromethane (1:1 to 0:1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-d454007496be4c219e01a1c84b3c8f19
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394836B2

Notizen zur Reaktion

Wird geladen…