Ammonium Chloride → HCID 58319265, compound

To a suspension of CH3PPh3I (664 mg, 1.64 mmol) in Et2O (20 mL) was added t-BuOK (184 mg, 1.64 mmol). The mixture was stirred for 15 minutes, to which was added dropwise 1-[3-(tert-butyl-dimethyl-silanyloxy)-5-trifluoromethyl-phenyl]-ethanone (436 mg, 1.37 mmol). The mixture was stirred at room temperature overnight and then diluted with Et2O. The mixture was filtered on a pad of celite. The residue compound was concentrated under reduced pressure. The crude residue was dissolved in THF and was added 1M-TBAF (in THF, 1.2 eq, 1.0M in CH2Cl2). The reaction mixture was stirred for 30 min at room temperature, treated with saturated ammonium chloride, and then extracted with EtOAc. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography to give 3-isopropenyl-5-trifluoromethyl-phenol (220 mg, 79%).

1. stirringThe mixture was stirred at room temperature overnight
2. filtrationThe mixture was filtered on a pad of celite
3. concentrationThe residue compound was concentrated under reduced pressure
4. dissolutionThe crude residue was dissolved in THF
5. stirringThe reaction mixture was stirred for 30 min at room temperature
6. extractionextracted with EtOAc
7. dry with materialThe organic layer was dried over magnesium sulfate
8. concentrationconcentrated in vacuo
9. customThe crude product was purified by column chromatography

ORD record

ord-a90623b9769b484d8c850f5c24f95d46

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691855B2