Potassium Carbonate → HCID 178418884, compound

HRID 860136Notes

Reaction equation

HRID 860136 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([CH3:16])[N:6](COCC[Si](C)(C)C)[CH:7]=1)#[CH:2].C(=O)([O-])[O-].[K+].[K+].[CH3:23][C:24]1[N:25](COCC[Si](C)(C)C)[CH:26]=[C:27]([CH:29]=O)N=1.[CH3:39]C1N(COCC[Si](C)(C)C)C(C=O)=CN=1>CO>[CH3:39][C:24]1[CH:23]=[C:29]([C:2]#[C:1][C:3]2[N:4]=[C:5]([CH3:16])[NH:6][CH:7]=2)[CH:27]=[CH:26][N:25]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 21198603HCID 21198603, compoundHCID 58765588HCID 58765588, compoundHCID 58765592HCID 58765592, compound

Product 1

HCID 178418884HCID 178418884, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-Ethynyl-2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole and 5-ethynyl-2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole(1-Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (10.4 g, 54 mmol) was dissolved in 150 mL methanol. Potassium carbonate (12.6 g, 90 mmol) was added. A solution of crude 2-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbaldehyde and 2-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazole-4-carbaldehyde (45 mmol) in 150 mmol methanol was added dropwise at RT. The reaction mixture was stirred at RT overnight. The solvent was evaporated. The residue was taken up in 150 mL water and extracted three times with ethyl acetate (150 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by column chromatography on silica gel (cyclohexane/ethyl acetate 1:1) and the desired compound was obtained as a mixture of 2 isomers (8.36 g, 78%), MS: m/e=237.0 (M+H+).

Workup

  1. customThe solvent was evaporated
  2. extractionextracted three times with ethyl acetate (150 mL each)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by column chromatography on silica gel (cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-d832a3ad5078400289d72c98d61c2de8
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Reaction notes

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