Dimethylformamide → 1,1'-Bis[[2-(trimethylsilyl)ethoxy]methyl]-2,2'-bi-1Himidazole
Reaction equation
[H-].[Na+].CN(C)[CH:5]=[O:6].[NH:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[NH:14][CH:15]=[CH:16][N:17]=1.[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23]Cl.CCCC[CH2:31][CH3:32]>>[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[N:17]([CH2:5][O:6][CH2:31][CH2:32][Si:19]([CH3:25])([CH3:20])[CH3:18])[CH:16]=[CH:15][N:14]=1Participants
Procedure
Under a blanket of nitrogen, 8.2 g (0.172 moles) 50% sodium hydride was washed with hexane. The flask was charged with 250 ml dry N,N-dimethylformamide and 11.5 g (0.086 moles) 2,2'-bi-1H-imidazole was added in small portions. After stirring at room temperature for 11/2 hours 30.8 g (0.185 moles) 2-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl) was added dropwise. The reaction exothermed slightly. The reaction was stirred for 1 hour then quenched with water and extracted into ethyl acetate (3×200 ml). The combined organic layers were shaken with water (2×300 ml), dried (anhydrous sodium sulfate) and concentrated to give 33.4 g tan oil. The product was purified by preparative HPLC (ethyl acetate) to give 26.9 g (79.2%) desired product as a light tan oil. A small portion was distilled. bp 260° C. at 0.2 mm.
Workup
- additionwas added in small portions
- additionwas added dropwise
- customthen quenched with water
- extractionextracted into ethyl acetate (3×200 ml)
- stirringThe combined organic layers were shaken with water (2×300 ml)
- dry with materialdried (anhydrous sodium sulfate)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-31ca59de303f4cc689ce59d7a45a9aaf
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05147863
Reaction notes
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