Dimethylformamide → 4-(4-Fluorophenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbaldehyde

HRID 983608Notes

Reaction equation

HRID 983608 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=2)=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:29]=[O:30])C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:29]=[O:30])[N:11]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 220185314-(4-Fluorophenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 220186684-(4-Fluorophenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbaldehyde

Procedure

Reaction of 4(4-fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (688 mg, 2.35 mmol), 1.5 M n-BuLi (2.0 mL, 3.0 mmol), and DMF (0.55 mL, 7.1 mmol) gave the title compound as a brown oil that was used without further purification in the next step. 1H NMR (CDCl3) 0.00 (s, 9H), 0.95 (m, 2H), 3.61 (m, 2H), 5.82 (s, 2H), 7.12 (m, 2H), 7.28 (s, 1H), 7.59 (s, 1H), 7.80. (m, 2H), 9.88 (s, 1H).

Sources & evidence

ORD record
ord-8637b9e766074cfe85e2393a8c6ff925
Source dataset
uspto-grants-2005_03
Patent number
US06864265B2

Reaction notes

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