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

HRID 892958

Reaction equation

HRID 892958 reaction equation
[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>[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

Participants

4

Reactant 2

HCID 12222Propynal2×HCID 148497764,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazole

Product 1

HCID 544077203-[4,5-Bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-2-propenal

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazole (492 mg) in dry THF under nitrogen was added propiolaldehyde (0.97 ml) and the reaction mixture heated to reflux. Further quantities of propiolaldehyde were added in portions (3×1.1 g) during successive 2 h periods. The reaction mixture was concentrated and the deep red residue was purified by FCC eluting with system A (1:4) to give the title product (398 mg) as an off-white solid and as a 1:1 mixture of geometric isomers. δ(CDCl3) 9.48 (d, 1H, J 7.5 Hz, cis CHO), 9.40 (d, 1H, J 7.5 Hz, trans CHO), 7.5 (d, 1H, J 15 Hz, trans CH=CHCHO), 7.45-6.85 (m, 17H, aromatic protons and cis CH=CHCHO), 5.98 (t,1H,J 7.5 Hz, cis CH=CHCHO), 5.63 (dd, 1H, J 15 and 7.5 Hz, trans CH=CH CHO), 3.25 (septet, 1H, J 7 Hz, CH(CH3)2 of trans isomer), 3.05 (septet, 1H, J 7 Hz, CH(CH3)2 of cis isomer).

Workup

  1. temperaturethe reaction mixture heated to reflux
  2. concentrationThe reaction mixture was concentrated
  3. customthe deep red residue was purified by FCC
  4. washeluting with system A (1:4)

Sources & evidence

ORD record
ord-3291c6b5848d497ebda6e597726f0724
Source dataset
uspto-grants-1992_06
Patent number
US05120848

Linked notes

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