Water → 4-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

HRID 1062589Notes

Reaction equation

HRID 1062589 reaction equation
IC1C=C2C(=CC=1)N(C)C(=O)N(C[C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1)C2=O.C(N(C(C)C)CC)(C)C.[C:34]([Si:38]([CH3:50])([CH3:49])[O:39]C1C=CC(CC#C)=CC=1)([CH3:37])([CH3:36])[CH3:35].O>CN(C=O)C.[Cu]I>[C:34]([Si:38]([CH3:50])([CH3:49])[O:39][C:15]1[CH:16]=[CH:17][C:18]([CH:19]=[O:21])=[CH:22][CH:23]=1)([CH3:37])([CH3:36])[CH3:35]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 11339553HCID 11339553, compoundHCID 22281868HCID 22281868, compound

Product 1

HCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To 0.65 g (1.5 mmol) 4-(6-Iodo-1-methyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-benzoic acid and 0.77 g (6.0 mmol) di-isopropyl ethylamine in 15 ml DMF is added bis-triphenylphosphine palladium di-chloride (catalytic) followed by CuI (catalytic). 0.5 g (2.0 mmol) tert-Butyl-dimethyl-(4-prop-2-ynyl-phenoxy)-silane is added and the mixture is heated to 70° C. for 6 hours. The mixture is allowed to cool to room temperature and stir overnight. Water is added and the mixture stirred 30 minutes. Filter and dry under reduced pressure. Purify by flash chromatography (EtOAc/hexane eluent)

Workup

  1. temperatureto cool to room temperature
  2. stirringthe mixture stirred 30 minutes
  3. filtrationFilter
  4. customdry under reduced pressure
  5. customPurify by flash chromatography (EtOAc/hexane eluent)

Sources & evidence

ORD record
ord-9ac556147ae54adf8346fe2946eb1aff
Source dataset
uspto-grants-2005_11
Patent number
US06962922B2

Reaction notes

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