Dimethylformamide → HCID 178441763, compound

HRID 36972Notes

Reaction equation

HRID 36972 reaction equation
CCCCCC.[H-].[Na+].[CH2:9]([C:13]1[NH:14][CH:15]=[CH:16][N:17]=1)[CH2:10][CH2:11][CH3:12].[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21]OCCl.CN(C)[CH:29]=[O:30]>>[CH2:9]([C:13]1[NH:14][CH:15]=[C:16]([CH2:29][O:30][CH:20]([Si:19]([CH3:18])([CH3:25])[CH3:26])[CH3:21])[N:17]=1)[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 8058HexaneHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 118153512-butyl-1H-imidazole

Product 1

HCID 178441763HCID 178441763, compoundYield 96%

Procedure

Hexane-washed 80% sodium hydride (1.45 g, 0.0483 mol) in dimethylformamide (80 mL) under argon was treated with a solution of 2-n-butylimidazole (5.45 g, 0.0439 mol) in dimethylformamide (14 mL) dropwise at 25° C. and the reaction was stirred an additional hour. Then 2-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl) (7.68 g, 0.0461 mol) was added, the mixture was stirred for 18 hours at ambient temperature and then partitioned between ice water and ethyl acetate. The washed, dried, concentrated organic solution was chromatographed over silica gel with 1:1 hexane in ethyl acetate to yield 10.8 g (96%) of 2-n-butyl-1-(trimethylsilyl)ethoxymethyl-imidazole.

Workup

  1. stirringthe mixture was stirred for 18 hours at ambient temperature
  2. custompartitioned between ice water and ethyl acetate
  3. customThe washed, dried
  4. customconcentrated organic solution was chromatographed over silica gel with 1:1 hexane in ethyl acetate

Sources & evidence

ORD record
ord-111714baa70c4b66a174c75f8b9f9764
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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