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

HRID 1072801Notes

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)ethoxymethyl)imidazol (29.2 g) was dissolved in tetrahydrofurane (250 ml) and a 1.63N n-butyl lithium/hexane solution (58.1 ml) was dropwise added over 20 min at −55° C. to −60° C. The mixture was stirred at −60° C. for 30 min and N,N-dimethylformamide (58 g) was dropwise added at −55° C. to −60° C., and 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 the objective compound (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-572f2c500e024985a4824cbcc8d2f6ec
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06911469B2

Reaction notes

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