Tetrahydrofuran → (E)-3-[4,5-Bis(4-fluorophenyl)-2-trifluoromethyl-1H-imidazol-1-yl]-2-propenal

HRID 892952Notes

Reaction equation

HRID 892952 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:24]([F:27])([F:26])[F:25])[N:11](/[CH:20]=[CH:21]/[C:22]#N)[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C1C[O:41]CC1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:24]([F:27])([F:26])[F:25])[N:11](/[CH:20]=[CH:21]/[CH:22]=[O:41])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14849771(E)-3-[4,5-Bis(4-fluorophenyl)-2-trifluoromethyl-1H-imidazol-1-yl]-2-propenenitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14849774(E)-3-[4,5-Bis(4-fluorophenyl)-2-trifluoromethyl-1H-imidazol-1-yl]-2-propenal

Procedure

From (E)-3-[4,5-bis(4-fluorophenyl)-2-trifluoromethyl-1H-imidazol-1-yl]-2-propenenitrile (484 mg) and diisobutylaluminum hydride (2.2 ml) in dry THF (15 ml) by the process as described for the preparation of Intermediate (4a) to afford a brown gum (0.53 g) which was purified by FCC eluting with System A (1:4) to afford the title compound (263 mg) as a yellow solid. νmax (Nujol) 1692 cm-1 (C=O).

Sources & evidence

ORD record
ord-af5ea4d0b9a847898b328afac30d1437
Source dataset
uspto-grants-1992_06
Patent number
US05120848

Reaction notes

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