2,2,2-Trifluoroethanol → HCID 178441287, compound

Participants

Reaction Steps

A mixture of the product from Example 47A (101 mg, 0.27 mmol), trifluoroethanol (33 mg, 0.32 mmol) and potassium tert-butoxide (2 M) (340 μL, 0.68 mmol) in THF (10 mL) was stirred at rt for 12 hrs. The mixture was diluted with water, and extracted with EtOAc. The organic extract was dried (Na2SO4), filtered and concentrated. The residue was purified by reverse phase preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile:0.1% aqueous trifluoroacetic acid over 8 minutes (10 minutes run time) at a flow rate of 40 mL/minute to afford 34 mg (28%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 0.97 (t, J=7.36 Hz, 3H) 1.37-1.48 (m, 2H) 1.65-1.75 (m, 2H) 1.68 (s, 9H) 4.50 (q, J=8.59 Hz, 2H) 7.05 (d, J=8.59 Hz, 1H) 7.34 (dd, J=8.90, 2.76 Hz, 1H) 7.97 (s, 1H) 8.11 (d, J=2.76 Hz, 1H); MS (DCI/NH4+) m/z 449 (M+H)+.

Provenance & Evidence