4-Hydroxybenzaldehyde → HCID 11403212, compound

HRID 492437Notes

Reaction equation

HRID 492437 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.N1C=CN=C1.[CH:15]([Si:18](Cl)([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16]>CN(C=O)C>[CH:15]([Si:18]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 795ImidazoleHCID 139400Triisopropylsilyl chloride

Product 1

HCID 11403212HCID 11403212, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Mix 4-hydroxybenzaldehyde (1.23 g, 10.1 mmol), imidazole (1.37 g, 20.2 mmol), and triisopropylsilyl chloride (2.60 mL, 12.1 mmol) in DMF (10 mL) and stir at room temperature for 2 hours. Quench the reaction with saturated aqueous NH4Cl (50 mL) and extract with EtOAc (3× 100 mL). Wash the organic layers with H2O and brine (50 mL each). Combine the organic layers, dry over MgSO4, concentrate and purify by flash chromatography, eluting with 2.5% Et2O/hexanes to afford 4-triisopropylsilyloxybenzaldehyde (2.78 g, 99%).

Workup

  1. customQuench
  2. customthe reaction with saturated aqueous NH4Cl (50 mL)
  3. extractionextract with EtOAc (3× 100 mL)
  4. washWash the organic layers with H2O and brine (50 mL each)
  5. dry with materialCombine the organic layers, dry over MgSO4
  6. concentrationconcentrate
  7. custompurify by flash chromatography
  8. washeluting with 2.5% Et2O/hexanes

Sources & evidence

ORD record
ord-dfcdd9f350a64837b6e97537078f4491
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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