Hydrochloric Acid → 3-(Trifluoromethyl)oxan-3-ol

Temperatur

0 °C

Tetrahydrofuran (50 mL) was added to a round bottom flask and placed under N2. trimethyl(trifluoromethyl)silane (1.033 mL, 6.99 mmol) was then added and stirred under N2 and then cooled to 0° C. Dihydro-2H-pyran-3(4H)-one (500 mg, 4.99 mmol) was then added via syringe and stirred for 5 minutes at 0° C. to ensure complete mixing. TBAF (0.050 mL, 0.050 mmol) was added dropwise slowly via syringe. The reaction was then allowed to warm up to RT for 30 min. The reaction was then cooled back down to 0° C. and added 1M HCl (50 mL) and then stirred at RT for overnight. The reaction was diluted with water and EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated to give the crude product 3-(trifluoromethyl)tetrahydro-2H-pyran-3-ol (400 mg, 47.1% yield) as an oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 4.01-3.93 (m, 1H), 3.82 (dd, J=11.8, 2.5 Hz, 1H), 3.60 (d, J=12.0 Hz, 1H), 3.41 (td, J=11.8, 2.5 Hz, 1H), 2.10-2.08 (m, 2H), 1.97-1.90 (m, 1H), 1.82 (dd, J=12.9, 4.4 Hz, 1H), 1.65-1.55 (m, 1H).

1. stirringstirred for 5 minutes at 0° C.
2. temperatureto warm up to RT for 30 min
3. temperatureThe reaction was then cooled back down to 0° C.
4. stirringstirred at RT for overnight
5. washThe organic layer was washed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated

ORD-Eintrag

ord-a6a81253c599439fb014bce1429a103d

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08957203B2