Imidazole → HCID 22345608, compound

HRID 584288Notes

Reaction equation

HRID 584288 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[C:6](=[CH:11][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8].[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].N1C=CN=C1>CN(C)C=O>[Si:17]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[C:6](=[CH:11][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22345632Dimethyl 4-hydroxymethylphthalate

Product 1

HCID 22345608HCID 22345608, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

19 g (84.8 mmol) of dimethyl 4-hydroxymethylphthalate are placed in 250 ml of dimethylformamide in a round-bottomed flask and under a stream of nitrogen. 14 g (93 mmol) of tert-butyldimethylsilyl chloride and 8 g (118 mmol) of imidazole are added. The reaction medium is stirred for 3 hours at room temperature, it is then concentrated and the residue is dissolved in ether and then filtered. The filtrate is evaporated and the product is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (50/50) to give 23.7 g (83%) of the expected product in the form of a yellow oil.

Workup

  1. concentrationit is then concentrated
  2. dissolutionthe residue is dissolved in ether
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. customthe product is purified by chromatography on a column of silica
  6. washeluted with a mixture of heptane and ethyl acetate (50/50)

Sources & evidence

ORD record
ord-955cdcedc30744ac8e18ecf9a6904fa8
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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