Hydrochloric Acid → HCID 50990625, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence