Imidazole → 2-(Tert-butyldiphenylsiloxy)-4-dibutylaminobenzaldehyde

HRID 85260Notes

Reaction equation

HRID 85260 reaction equation
[CH2:1]([N:5]([CH2:15][CH2:16][CH2:17][CH3:18])[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([OH:14])[CH:7]=1)[CH2:2][CH2:3][CH3:4].N1C=CN=C1.[C:24]([Si:28](Cl)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:27])([CH3:26])[CH3:25].O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([N:5]([CH2:15][CH2:16][CH2:17][CH3:18])[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([O:14][Si:28]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 185345344-(Dibutylamino)salicylaldehyde

Product 1

HCID 866676032-(Tert-butyldiphenylsiloxy)-4-dibutylaminobenzaldehydeYield 97.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 40 ml of N,N-dimethylformamide were dissolved 5.39 g (21.6 mmol) of 4-dibutylamino-2-hydroxybenzaldehyde and 4.08 g (60.0 mmol) of imidazole. Next, 6.13 g (22.3 mmol) of tert-butylchlorodiphenylsilane was added dropwise thereto with stirring at room temperature. The mixture was stirred for 3.5 hours. After the reaction mixture was poured into water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give 10.3 g of a colorless oily matter (yield: 97.7%).

Workup

  1. stirringThe mixture was stirred for 3.5 hours
  2. washwashing with a saturated saline solution
  3. dry with materialdrying over anhydrous sodium sulfate, and concentration
  4. customThe residue was purified by silica gel column chromatography
  5. customto give 10.3 g of a colorless oily matter (yield: 97.7%)

Sources & evidence

ORD record
ord-7d6688445c8a4f84886fc5a5b8c445e0
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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