Imidazole → HCID 86647421, compound

HRID 2070990Notes

Reaction equation

HRID 2070990 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=[O:11])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[CH3:19][C:20]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])[CH3:21]>CN(C=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:13][Si:23]([C:20]([CH3:22])([CH3:21])[CH3:19])([CH3:25])[CH3:24])=[C:9]([CH:12]=1)[CH:10]=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 14750905-tert-Butylsalicylaldehyde

Product 1

HCID 86647421HCID 86647421, compoundYield 114.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-tert-butyl-2-hydroxybenzaldehyde (570 mg, 3.2 mmol) in DMF (5 mL) was added imidazole (435 mg, 6.4 mmol) and TBSCl (576 mg, 3.8 mmol). The reaction mixture was stirred for 15 h and quenched with saturated aqueous NH4Cl. The resulting mixture was extracted with EtOAc (2×20 mL). The combined organic layer was washed with H2O, brine, dried with Na2SO4 and concentrated under reduced pressure to provide 5-tert-butyl-2-(tert-butyldimethylsilyloxy)benzaldehyde (1.07 g, quantitative).

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionThe resulting mixture was extracted with EtOAc (2×20 mL)
  3. washThe combined organic layer was washed with H2O, brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d911cdc494948caa7f12b9a8afadba8
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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