Dimethylformamide → 2-Fluoro-1-trityl-1H-imidazole-4-carbaldehyde

HRID 1463164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1463164
[F:1][C:2]1[N:3]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1.C([Li])(C)(C)C.CN([CH:34]=[O:35])C>C1COCC1.CCCCC.CCOCC>[CH:34]([C:5]1[N:6]=[C:2]([F:1])[N:3]([C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:4]=1)=[O:35]

Komponenten

7

Edukt 3

HCID 6228DimethylformamideHCID 20432454HCID 20432454, VerbindungHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 537790282-Fluoro-1-trityl-1H-imidazole-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-fluoro-1-triphenylmethylimidazole (3.28 g.) in dry THF (33 ml.) was treated, under argon, at -75° with two equivalents of t-butyl lithium (10 ml. of a 1.93M solution in pentane). After stirring 3 hours at -75°, DMF (1.5 ml.) was added. The reaction mixture was kept a further hour at -75° then allowed to warm up slowly to room temperature. The reaction was worked up by diluting with ether, washing with 2N HCl followed by brine. The ether layer was concentrated under a steam of argon to give 4-formyl-2-fluoro-1-triphenylmethylimidazole, (2.2 g.) m.p. 177°-179°.

Aufarbeitung

  1. waitThe reaction mixture was kept a further hour at -75°
  2. washwashing with 2N HCl
  3. concentrationThe ether layer was concentrated under a steam of argon

Quellen und Nachweise

ORD-Eintrag
ord-8cdc0af79e5c409da9b8245fc4fa6fcf
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04463173

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