Dimethylformamide → 4-Bromo-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)imidazole-5-carbaldehyde

HRID 1828790Notes

Reaction equation

[Br:1][C:2]1[N:3]=[C:4]([CH3:16])[N:5]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1Br.C([Li])CCC.CCCCCC.CN(C)[CH:30]=[O:31]>O1CCCC1.[Cl-].[Na+].O>[Br:1][C:2]1[N:3]=[C:4]([CH3:16])[N:5]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[CH:30]=[O:31]

Participants

Conditions

Temperature: -60 °C

Procedure

4,5-Dibromo-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)imidazole (29.2 g) was dissolved in tetrahydrofuran (250 ml), and 1.63N 1-butyl lithium/hexane solution (58.1 ml) was added dropwise over 20 min at from −55° C. to −60° C. The mixture was stirred at −60° C. for 30 min and N,N-dimethylformamide (58 g) was gradually added dropwise at from −55° C. to −60° C. The mixture was stirred at room temperature for 1 hr. Saturated brine was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to give 4-bromo-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-imidazole-5-carbaldehyde (18.5 g) as a pale-yellow oil.

Workup

stirringThe mixture was stirred at room temperature for 1 hr
extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-4d680cf617a14265aa481713b6ba2a56
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060721B1

Reaction notes

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