Propynal → (E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-2-propenal

HRID 2050579

Reaktionsgleichung

Reaktionsgleichung von HRID 2050579
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:20]([CH3:22])[CH3:21])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH:23](=[O:26])[C:24]#[CH:25]>C1COCC1.CC(C)=O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:11]=[C:10]([CH:20]([CH3:22])[CH3:21])[N:9](/[CH:25]=[CH:24]/[CH:23]=[O:26])[C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:14][CH:15]=1

Komponenten

5

Edukt 2

HCID 12222PropynalHCID 148497764,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazole

Produkt 1

HCID 14849786(E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-2-propenal

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazole (200 mg) and propiolaldehyde (75% solution in toluene, 0.15 ml) in dry THF (15 ml) were heated under reflux, under nitrogen for 24 h. The residue was dissolved in acetone and absorbed onto silica gel before purifying by CC eluting with petroleum ether (b.p. 40°-60°)/ethyl acetate (2:1) to give the title compound (84 mg) as a pale yellow solid, δ(CDCl3), 1.49 (d, J=7 Hz, Me2CH), 3.25 (septet, J=7 Hz, Me2CH), 5.67 (dd, J=15 Hz, 7 Hz, CH=CH.CHO), 6.95 and 7.10-7.60 (t, J=9 Hz and m, CH=CH.CHO and aromatic protons), 9.40 (d, J=7 Hz, CH=CH.CHO).

Aufarbeitung

  1. temperatureunder reflux, under nitrogen for 24 h
  2. customabsorbed onto silica gel
  3. custombefore purifying by CC
  4. washeluting with petroleum ether (b.p. 40°-60°)/ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-5322d1d63ca74e688924c062f834ef93
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05013749

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