Dimethylformamide → HCID 17875574, compound

HRID 377233Notes

Reaction equation

HRID 377233 reaction equation
CCCC[CH2:5][CH3:6].[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](C)([CH3:25])[CH2:20]COCCl.CN(C)[CH:29]=[O:30]>>[CH2:9]([C:13]1[N:14]([Si:19]([CH3:25])([CH3:20])[CH3:18])[CH:15]=[C:16]([CH2:29][O:30][CH2:5][CH3:6])[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 17875574HCID 17875574, 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-68a90fd6e79d4b2da6e8240999a83d17
Source dataset
uspto-grants-2000_02
Patent number
US06025380

Reaction notes

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