Water → HCID 14410054, compound

HRID 1383836Notes

Reaction equation

HRID 1383836 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[NH:14][CH:13]=[N:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:15]([Li])CCC.IC.O>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[N:14]=[CH:13][N:12]([CH3:15])[CH:11]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3].[Si:1]([O:8][CH2:9][C:10]1[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14410052HCID 14410052, compoundHCID 178418339Butyllithium

Product 2

HCID 14410053HCID 14410053, compoundYield 14%HCID 14410054HCID 14410054, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-(tert-butyldimethylsilanyloxymethyl)-1H-imidazole (Amino, Y.; Eto, H.; Eguchi, C., Chem. Pharm. Bull., 1989, 37, 1481-1487) (3.158 g, 14.9 mmol) in anhydrous THF (25 ml), cooled to −78° C. under nitrogen, was added a 1.6 M solution of butyllithium in hexanes (10.2 ml, 16.4 mmol). The mixture was stirred under nitrogen at −78° C. for 30 min, then iodomethane (0.97 ml, 15.6 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 5 h. Water (150 ml) was then added and the mixture was extracted with diethyl ether (150 ml). The organic extract was washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (alumina, 40% EtOAc/hexane) to yield 0.4732 g (14%) of 4-(tert-butyldimethylsilanyloxymethyl)-1-methyl-1H-imidazole and 1.463 g (43%) of 5-(tert-butyldimethylsilanyloxymethyl)-1-methyl-1H-imidazole.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 5 h
  3. extractionthe mixture was extracted with diethyl ether (150 ml)
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography (alumina, 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-7946d706d7634f2fbeb2a1d4eec68ba2
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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