Imidazole → 2,5-Dimethyl-4-triisopropylsilanyloxy-benzaldehyde

HRID 2108602Notes

Reaction equation

HRID 2108602 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].N1C=CN=C1.Cl[Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20]>CN(C=O)C>[CH3:1][C:2]1[CH:9]=[C:8]([O:10][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[C:7]([CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 128272904-Hydroxy-2,5-dimethyl-benzaldehyde

Product 1

HCID 860521872,5-Dimethyl-4-triisopropylsilanyloxy-benzaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 2,5-dimethyl-4-hydroxy-benzaldehyde (0.43 g, 2.86 mmol) in DMF (8 mL) at room temperature was added imidazole (0.43 g, 6.29 mmol) and chloro-triisopropyl-silane (0.74 mL, 3.43 mmol). The mixture was stirred at room temperature for 16 hrs. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (15:75) to afford 2,5-dimethyl-4-triisopropylsilanyloxy-benzaldehyde as a colorless oil (0.7 g, 80%): 1H NMR (300 MHz, DMSO-d6): δ 10.07 (s, 1H), 7.65 (s, 1H), 6.69 (s, 1H), 2.55 (s, 3H), 2.21 (s, 3H), 1.35 (m, 3H), 1.10 (d, J=6.9 Hz, 18H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=5% ethyl acetate in hexanes; Rf=0.68.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel
  7. washeluting with ethyl acetate-hexanes (15:75)

Sources & evidence

ORD record
ord-7b9c72e260d0450d9d86b2cd89d675b7
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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