HCID 86654777, compound → HCID 67111134, compound

HRID 2363122Notes

Reaction equation

HRID 2363122 reaction equation
[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][C:7]1[CH:8]=[C:9]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1)[C:10](N(OC)C)=[O:11])([CH3:4])([CH3:3])[CH3:2].[CH3:25][Mg]Cl>C1COCC1.CCOCC>[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][C:7]1[CH:8]=[C:9]([C:10](=[O:11])[CH3:25])[CH:16]=[C:17]([C:19]([F:21])([F:20])[F:22])[CH:18]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 86654777HCID 86654777, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 67111134HCID 67111134, compoundYield 99,950.203%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold suspension of 3-(tert-butyl-dimethyl-silanyloxy)-N-methoxy-N-methyl-5-trifluoromethyl-benzamide (500 mg, 1.37 mmol) in THF (5 mL) was added dropwise 3.0M CH3MgCl (687 mL, 2.06 mmol) at 0° C. The mixture was stirred for 3 hours at room temperature, and then diluted with Et2O. The reaction mixture was washed with saturated ammonium chloride, water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography to give 1-[3-(tert-butyl-dimethyl-silanyloxy)-5-trifluoromethyl-phenyl]-ethanone (436 g, 99%).

Workup

  1. washThe reaction mixture was washed with saturated ammonium chloride, water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-86f8e9e394b24245bcf8f64d42f0826d
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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