Dimethylformamide → 5-(3,5-Dimethylphenylthio)-4-ethyl-2-methyl-1-trimethylsilyloxyethoxymethyl-imidazole
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][C:13]([CH3:15])=[N:12][C:11]=2[CH2:16][CH3:17])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[H-].[Na+].[CH3:20][Si:21]([CH3:29])([CH3:28])[O:22][CH2:23][CH2:24]OCI.CN(C)[CH:32]=[O:33]>>[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:32][O:33][CH:23]([O:22][Si:21]([CH3:20])([CH3:28])[CH3:29])[CH3:24])[C:13]([CH3:15])=[N:12][C:11]=2[CH2:16][CH3:17])[CH:5]=[C:6]([CH3:8])[CH:7]=1Participants
Procedure
To a solution of 500 mg of 5-(3,5-dimethylphenylthio)-4-ethyl-2-methylimidazole (2 mmol) in 5 ml of dry dimethylformamide is added 120 mg of 60% oil suspension of sodium hydride (3 mmol) under ice cooling and allowed to stand for 5 minutes. After the addition of 820 mg of iodomethyl trimethylsilyloxyethyl ether (3 mmol) [Tetrahydron Letters, No. 35, pp. 3263-3264, 1979], the mixture is allowed to stand for 15 minutes, when it is poured onto ice water and extracted with ethyl ether. The extract is washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is chromatographed on a column of silica gel, eluting with ethyl acetate/n-hexane (2:1) to give 170 mg of 5-(3,5-dimethylphenylthio)-4-ethyl-2-methyl-1-trimethylsilyloxyethoxymethyl-imidazole 4 as an oil. Yield, 21%.
Workup
- waitto stand for 15 minutes
- additionwhen it is poured onto ice water
- extractionextracted with ethyl ether
- washThe extract is washed with water
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue is chromatographed on a column of silica gel
- washeluting with ethyl acetate/n-hexane (2:1)
Sources & evidence
- ORD record
- ord-ce8802621c7d4968977524ee4255d245
- Source dataset
- uspto-grants-1995_12
- Patent number
- US05472965
Reaction notes
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