Imidazole → HCID 11843644, compound

HRID 2223057Notes

Reaction equation

HRID 2223057 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].N1C=CN=C1>CN(C)C=O>[Si:14]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 3442904-Hydroxy-1-naphthaldehyde

Product 1

HCID 11843644HCID 11843644, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxynaphthalene-1-carbaldehyde (2.00 g, 11.63 mmol), tert-butyldimethylsilyl chloride (1.93 g, 12.80 mmol), imidazole (983 mg, 15.12 mmol) and N,N-dimethylaminopyridine (4 mg) in N,N-dimethylformamide (20 ml) were stirred at RT for 20 h. The solvent was removed and the mixture suspended in ethyl acetate (20 ml) and washed with water (20 ml). The aqueous phase was extracted with ethyl acetate (20 ml) and the combined organics washed with brine (2×20 ml) and dried (MgSO4). The solvent was removed leaving the product as a brown oil which solidified on standing.

Workup

  1. customThe solvent was removed
  2. washwashed with water (20 ml)
  3. extractionThe aqueous phase was extracted with ethyl acetate (20 ml)
  4. washthe combined organics washed with brine (2×20 ml)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-5e4cbb45b9434e7a9936d843467a79e8
Source dataset
uspto-grants-2008_05
Patent number
US07375100B2

Reaction notes

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