Triethylamine → HCID 19024579, compound
Reaction equation
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[C:7]([CH2:12][OH:13])=[C:8]([CH2:10][OH:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[Si:29](Cl)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[C:7]([CH2:12][OH:13])=[C:8]([CH2:10][O:11][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[N:9]=1)[CH2:2][CH2:3][CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 25 °C
Procedure
A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-4,5-bis (hydroxy)methyl-1H-imidazole (Example 1 (ii)) (310 mg, 1 mmol) in methylene chloride (5 mL) was treated with 4-dimethylaminopyridine (5.2 mg), triethylamine (1.5 mmol) and t-butyl dimethylsilyl chloride (192 mg, 1.24 mmol). The mixture was stirred at 25° C. for 20 hours, diluted with water and the organic layer was washed well with water, dried, concentrated and chromatographed over silica gel with an ethyl acetate/methanol gradient to afford 127 mg (24%) of the bis (4,5-t-butyldimethylsilyl) ether and 252 mg (59%) of 2-n-butyl-1-(2-chlorophenyl)methyl-4-t-butyldimethysilyloxymethyl-5-hydroxymethyl-1H-imidazole. This monoether (252 mg) was oxidized to the 5-carbox-aldehyde using manganese dioxide as described in Example 1 (iii) to provide 170 mg of 2-n-butyl-1-(2-chlorophenyl)-methyl-4-(t-butyldimethylsilyloxy)methyl-1H-imidazol-5-carboxaldehyde as an oil.
Workup
- washthe organic layer was washed well with water
- customdried
- concentrationconcentrated
- customchromatographed over silica gel with an ethyl acetate/methanol gradient
Sources & evidence
- ORD record
- ord-b8bd110a9ae9493f95dbfbc95779eb8c
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05418250
Reaction notes
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