Imidazole → HCID 18182319, compound

HRID 1359275Notes

Reaction equation

HRID 1359275 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:5][CH:4]=1.N1C=CN=C1.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]>CN(C)C=O>[C:9]([C:7]1[C:6]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:5][CH:4]=[C:3]([CH2:2][O:1][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[N:8]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18182256HCID 18182256, compound

Product 1

HCID 18182319HCID 18182319, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

116 g of 6-hydroxymethyl-2-benzoyl-3-benzyloxypyridine was dissolved in 450 ml of N,N-dimethylformamide. 100 g of imidazole and 85 g of tert-butyldimethylsilyl chloride was added thereto, followed by stirring at room temperature overnight. The solvent was removed, water was added thereto and the mixture was extracted with ethyl acetate. Further, the organic phase was washed with dilute hydrochloric acid, water, an aqueous saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was dried, to give 141 g of the target compound.

Workup

  1. customThe solvent was removed
  2. additionwater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washFurther, the organic phase was washed with dilute hydrochloric acid, water
  5. dry with materialan aqueous saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was dried

Sources & evidence

ORD record
ord-1615ed1c384e4bbb855b8f198c3484c9
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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