[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[CH:5][C:4]=1[CH:14]=[O:15])[CH3:2].[CH3:16][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1.CCOCC>[CH2:1]([C:3]1[N:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:6]=[CH:5][C:4]=1[CH:14]([OH:15])[CH3:16])[CH3:2]To a 0° C. solution of 7.55 (37.7 mmol) of 5-ethyl-1-phenyl-1H-pyrazole-4-carbaldehyde (Example 86) in anhydrous THF (100 mL) under N2 was added over 5 minutes 15.7 (47.1 mmol) of 3.0 M MeMgBr in Et2O. The mixture was warmed to room temperature and stirred for 16 h, then 25 mL of 5% NH4Cl was added and the mixture was extracted with CH2Cl2 (70 mL), and the extract was washed with saturated NaCl (15 mL). The organic layer separated, dried over MgSO4, and concentrated to give 1-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-ethanol (7.91 g). ESI MS m/z 217 [C13H16N2O+H]+.
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