Imidazole → HCID 18953767, compound

HRID 1492021Notes

Reaction equation

HRID 1492021 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:7].N1C=CN=C1.[Si:19](Cl)([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.O>[Si:19]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 14576266HCID 14576266, compound

Product 1

HCID 18953767HCID 18953767, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4.59 g (0.0256 mole) of 5-hydroxy-1-(3-pyridyl)pentan-1-one, 3.82 g (0.0561 mole) of imidazole 7.76 g (0.0282 mole) of tert-butyldiphenylsilylchloride in 10 ml of dimethylformamide is stirred at room temperature for 15 h, diluted with 75 ml of water and extracted with ethyl acetate (2×50 ml). The extracts are washed with water and brine, dried (MgSO4) and evaporated. The residue is purified by flash chromatography using methylene chloride-ethyl acetate (4:1) as eluent to give 5-(t-butyldiphenylsilyloxy)-1-(3-pyridyl)pentan-1-one as an oil.

Workup

  1. extractionextracted with ethyl acetate (2×50 ml)
  2. washThe extracts are washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-6f250b4ff3b44ccf94ba2b3361c52b00
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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