Sodium Iodide → N1-[5-Acetyl-3-(tert-butyl)-2-hydroxyphenyl]acetamide

HRID 1295996Notes

Reaction equation

HRID 1295996 reaction equation
Cl[Si](C)(C)C.[C:6]([C:9]1[CH:10]=[C:11]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:12]([O:19]COC)=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[CH:14]=1)(=[O:8])[CH3:7].[I-].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[C:6]([C:9]1[CH:10]=[C:11]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:12]([OH:19])=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[CH:14]=1)(=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 58910001N1-[5-Acetyl-3-(tert-butyl)-2-(methoxymethoxy)phenyl]acetamide

Product 1

HCID 58910050N1-[5-Acetyl-3-(tert-butyl)-2-hydroxyphenyl]acetamideYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chlorotrimethylsilane (36.5 ml, 288 mmol) was added dropwise to a solution of the N1-[5-acetyl-3-(tert-butyl)-2-(methoxymethoxy)phenyl]acetamide (56.2 g, 192 mmol) and sodium iodide (43.1 g, 288 mmol) in tetrahydrofuran (300 ml) under a nitrogen atmosphere while cooling on ice, and then the mixture was stirred at the same temperature for 10 minutes and at room temperature for 1 hour. The reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate (400 ml)-ice (300 ml) mixed solvent while stirring. Following extraction twice with ethyl acetate, the organic layer was washed with saturated aqueous sodium hydrogencarbonate and brine in that order. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate-n-hexane to yield the title compound (first crystallization=30.5 g, second crystallization=3.55 g, 71.3% yield) as white needle-like crystals.

Workup

  1. temperaturewhile cooling on ice
  2. additionmixed solvent
  3. stirringwhile stirring
  4. extractionextraction twice with ethyl acetate
  5. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate and brine in that order
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-0db4bfe286d94614994f42bdbbdb8fd7
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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