Ammonium Chloride → 5-Ethynyl-1-methyl-4-phenyl-1H-imidazole

HRID 32535Notes

Reaction equation

[CH2:1]([Li])CCC.C[Si](C=[N+]=[N-])(C)C.[CH3:13][N:14]1[C:18]([CH:19]=O)=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:16]=[CH:15]1.[Cl-].[NH4+]>C1COCC1>[C:19]([C:18]1[N:14]([CH3:13])[CH:15]=[N:16][C:17]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)#[CH:1]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (2M in pentane, 650 μL) was added dropwise to trimethylsilyldiazomethane (2M in hexane, 750 μL) in THF (1 mL), cooled to −78° C. and stirred for 30 minutes. 1-Methyl-4-phenyl-1H-imidazole-5-carbaldehyde (intermediate 2) (186 mg) was added dropwise over 5 minutes and stirring continued at −78° C. for 30 minutes, then warmed to 0° C. over 30 minutes and stirred for a further 30 minutes at 0° C. Saturated aqueous ammonium chloride (3 mL) was added, mixture extracted with diethyl ether (3×5 mL), organics combined dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with DCM:MeOH (50.1) afforded the title compound as yellow solid (61.3 mg, 34%);

Workup

stirringstirring
waitcontinued at −78° C. for 30 minutes
temperaturewarmed to 0° C. over 30 minutes
stirringstirred for a further 30 minutes at 0° C
extractionmixture extracted with diethyl ether (3×5 mL)
dry with materialorganics combined dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by flash chromatography on silica eluting with DCM

Sources & evidence

ORD record: ord-16adfa7b8a76456dba343ce64526da90
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427616B2

Reaction notes

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