Ammonium Chloride → 8-(Trifluoromethyl)-1,4-dioxaspiro[4.5]decan-8-ol

1,4-cyclohexandione mono-ethylene ketal (1.5 g, 9.6 mmol) was dissolved in THF (35 ml), followed by sequential addition of trimethyl(trifluoromethyl)silane (2.8 ml, 19.2 mmol) and tetrabutylammonium fluoride (1.0M solution in THF, 20 ml, 20.0 mmol) at 0° C., and then the resulting mixture was stirred at room temperature for 2 hours. A saturated aqueous ammonium chloride solution (10 ml) was added to the resulting reaction liquid, and then, the resulting mixture was stirred for 10 minutes, followed by concentration under reduced pressure. Distilled water (10 ml) was added to the residue thus obtained, followed by extraction with MC (50 ml×2). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (40% EtOAc/Hexanes), to obtain 2.1 g of yellow oil (97%).

1. stirringthe resulting mixture was stirred for 10 minutes
2. concentrationfollowed by concentration under reduced pressure
3. additionDistilled water (10 ml) was added to the residue
4. customthus obtained
5. extractionfollowed by extraction with MC (50 ml×2)
6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
7. filtrationfollowed by filtration and concentration
8. customthe residue thus obtained

ORD record

ord-074953bd5b164d4c9d1a4c6fb4ad5f30

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096571B2