(Trifluoromethyl)trimethylsilane → 3-Methyl-5-[4-(2,2,2-trifluoro-1-hydroxy-ethyl)-pyridin-3-yl]-3H-benzooxazol-2-one

Participants

Reaction Steps

A solution of TBAF in THF (1M, 0.02 mL, 0.02 mmol) was added dropwise to a mixture of 3-(3-Methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-4-carbaldehyde (54 mg, 0.21 mmol) and (trifluoromethyl)trimethyl silane (0.2 mL, 0.42 mmol) in THF (0.8 mL) at 5° C. under nitrogen. After 5 min at this temperature, TBAF (1M in THF, 1 mL, 1 mmol) was added. The resulting solution was diluted with ethyl acetate and water. The organic layer was washed with brine and dried over anhydrous Na2O4. After concentration, the residue was purified by PTLC (10% MeOH in DCM, v/v) gave 3-Methyl-5-[4-(2,2,2-trifluoro-1-hydroxy-ethyl)-pyridin-3-yl]-3H-benzooxazol-2-one. (13 mg, 19%); ESI-MS m/z: 325 [M+1]+, Retention time 1.53 min; 1H-NMR (MeOD, 400 MHz) δ 8.65 (1H, d, 5.6 Hz), 8.50 (1H, s), 7.79 (1H, d, J=5.6 Hz), 7.39 (1H, d, J=8.0 Hz), 7.17 (1H d, J=1.6 Hz), 7.12 (1H, dd, J=8.0, 1.6 Hz), 5.16 (1H, q, J=6.8 Hz), 3.43 (3H, s).

Provenance & Evidence