Dimethyl Sulfide → HCID 136176946, compound

Participants

Reaction Steps

To a solution of 4-(5-(2-(tert-butyldimethylsilyloxy)ethyl)-3-(4-methoxyphenyl)-1-methyl-1H-pyrazol-4-yl)-3,5-dimethylisoxazole (41.5 mg, 0.094 mmol) in DCM (3 ml) was added BF3.Me2S (1 M solution in DCM, 0.5 mL, 0.5 mmol) and the mixture was stirred at room temperature over night. The DCM layer was discarded and the precipitate was washed with another 0.2 ml DCM. The raw product was purified on silica gel to give 4-(4-(3,5-dimethylisoxazol-4-yl)-5-(2-hydroxyethyl)-1-methyl-1H-pyrazol-3-yl)phenol (28.6 mg, 0.091 mmol, 97%) ES/MS m/z: 314.22 (M+H), 312.31 (M−H); 1H NMR (MeOD, 500 MHz): 7.15 (m, 2H), 6.70 (m, 2H), 3.88 (s, 3H), 3.54 (t, 2H, J=6.8 Hz), 2.70 (t, 2H, J=6.8 Hz), 2.16 (s, 3H) and 1.87 (s, 3H).

Provenance & Evidence