Acetic Acid → HCID 18409499, compound

Participants

Reaction Steps

A mixture of 5-(4-(methylsulphonyl)phenyl)-4-phenyl-3-trimethylacetylmethoxy-pyrazole prepared according to the Example 32B [(100 mg, 0.24 mmol), p-toluenesulfonic acid hydrate (25 mg) in toluene (40 mL), and acetic acid (15 mL) was refluxed using a Dean-Stark trap to remove water, for 12 hours. The reaction mixture was concentrated in vacuo and the residue chromatographed (silica gel, 1:1 hexane/ethyl acetate) to provide the desired product (yield: 97 mg; 99%). MP 187-180° C.; MS (APCI+) m/z 395 (M+H)+; (APCI−) m/z 393 (M−H)−, 429 (M+Cl)−; 1H NMR (300 MHz, DMSO-d6) δ1.49 (s, 9H), 3.25 (s, 3H), 7.35 (m, 5H), 7.76 (d, J=9 Hz, 2H), 7.95 (s+d, J=9 Hz, 3H); Anal. calc. for C22H22N2O3S.0.5 H2O: C, 65.48; H, 5.74; N, 6.94. Found: C, 65.70; H, 5.69; N, 6.65.

Provenance & Evidence