Hydrochloric Acid → HCID 50990625, compound

Temperature

0 °C

Tetrahydrofuran (55 mL) was added to a round bottom flask and placed under N2. trimethyl(trifluoromethyl)silane (2.404 mL, 16.26 mmol) was then added and stirred under N2 and then cooled to 0° C. Dihydrofuran-3(2H)-one (1 g, 11.62 mmol) was then added via syringe and stirred for 5 minutes at 0° C. to ensure complete mixing. TBAF (0.116 mL, 0.116 mmol) was added dropwise slowly via syringe and allowed to warm up to RT for 1 hr. The reaction was then cooled back down to 0° C. and added 30 mL of 1N HCl and stirred at RT for overnight. The reaction was then diluted with EtOAc and separated with water. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated to give the product 3-(trifluoromethyl)tetrahydrofuran-3-ol (800 mg, 44.1% yield) as an orange thin oil. 1H NMR (400 MHz, CHLOROFORM-d) d 4.05-3.92 (m, 3H), 3.80-3.75 (m, 1H), 2.31 (dt, J=13.3, 8.4 Hz, 1H), 2.08-2.03 (m, 1H).

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

ORD record

ord-7ec29d0271884a69b027997a669795f6

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957203B2