Methane, dichloromethoxy- → Cyclopropylmethyl [3-methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetate
Reaction equation
ClC(Cl)OC.[CH3:6][C:7]1[C:11]([CH2:12][C:13]([OH:15])=[O:14])=[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:9]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][C:27]=2[CH3:28])[N:8]=1.[CH:29]1([CH2:32]O)[CH2:31][CH2:30]1>>[CH3:6][C:7]1[C:11]([CH2:12][C:13]([O:15][CH2:32][CH:29]2[CH2:31][CH2:30]2)=[O:14])=[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:9]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][C:27]=2[CH3:28])[N:8]=1Participants
4
Conditions
- Temperature
- 60 °C
Procedure
0.296 g (2.575 mmol) of dichloro(methoxy)methane was added to 0.175 g (0.569 mmol) [3-methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetic acid, and the mixture was stirred at 60° C. for 2 h. Excess dichloro(methoxy)methane was removed under reduced pressure, 0.660 g (9.153 mmol) of cyclopropylmethanol was added to the residue and the mixture was stirred at 20° C. for 0.5 h. The solvent was removed under reduced pressure, a mixture of 10 ml of dichloromethane, 1.5 ml of diisopropylethylamine and 10 ml of water was added to the residue and the aqueous phase was extracted with 15 ml of dichloromethane. The combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. Chromatography of the residue gave 0.123 g (59% of theory) of a colorless solid of m.p. 87° C.