Triacetoxyperiodinane → HCID 86732041, compound

Participants

Reaction Steps

To a stirred solution of trans-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)cyclopropyl)methanol (16-5, 409 mg, 1.30 mmol, 1.0 eq.) in anhydrous DCM (10.0 mL) at 0° C. was added Dess-Martin periodinane (610 mg, 1.44 mmol, 1.1 eq.). The resulting mixture was stirred for 2 hours at room temperature under an atmosphere of nitrogen gas. The mixture was then quenched with saturated aqueous NaHCO3 solution (10 mL) and 10% aqueous Na2S2O3 solution (10 mL) and vigorously stirred at room temperature for 1 hour until it formed a clear two phase solution. The separated aqueous layer was extracted with DCM (2×50 mL). The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The resulting residue was purified by silica gel column chromatography (0-50% ethyl acetate in hexanes) to give trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)cyclopropanecarbaldehyde (16-6) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 9.55 (d, 1H, J=3.6 Hz), 7.99 (s, 1H), 2.92 (s, 3H), 2.86-2.73 (m, 2H), 2.43 (s, 3H), 1.97 (ddd, 1H, J=9.9, 5.7, 4.2 Hz), 1.85 (ddd, 1H, J=9.9, 5.7, 4.2 Hz). LRMS m/z (M+H) 312 found, 312 required.

Provenance & Evidence