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

HRID 983606Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3]1[N:4]=[CH:5][N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=1.[Li]CCCC.CN([CH:26]=[O:27])C>>[F:17][C:2]([F:16])([F:1])[C:3]1[N:4]=[C:5]([CH:26]=[O:27])[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:13])([CH3:14])[CH3:15])[CH:7]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 136002324-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole

HCID 178418339Butyllithium

Product 1

HCID 220187654-Trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbaldehydeYield 14.2%

Procedure

Reaction of 4-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (590 mg, 2.2 mmol), 2.3 M n-BuLi (1.3 mL, 3.0 mmol), and DMF (0.51 mL, 6.6 mmol) followed by purification of the crude material on silica gel (10% EtOAc/hexanes) gave the title compound as a yellow oil (92 mg, 14% over two steps). 1H NMR (CDCl3) □0.02 (s, 9H), 0.95 (m, 2H), 3.60 (m, 2H), 5.79 (s, 2H), 7.28 (s, 1H), 7.67 (s, 1H), 9.86 (s, 1H).

Workup

customfollowed by purification of the crude material on silica gel (10% EtOAc/hexanes)

Sources & evidence

ORD record: ord-0372b6c54ecd42a3a7f6af1de94ccccf
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864265B2

Reaction notes

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