METHYL 4-(1H-PYRAZOL-1-YLMETHYL)BENZOATE synthesis
- Product Name:METHYL 4-(1H-PYRAZOL-1-YLMETHYL)BENZOATE
- CAS Number:397328-86-8
- Molecular formula:C12H12N2O2
- Molecular Weight:216.24
2417-72-3
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Yield:397328-86-8 92%
Reaction Conditions:
with NH-pyrazole;NaH in (2S)-N-methyl-1-phenylpropan-2-amine hydrate;N,N-dimethyl-formamide;
Steps:
166.1 (166-1)
(166-1) Under nitrogen atmosphere, a solution of pyrazole (743 mg) in DMF (10 mL) was cooled to 0° C., and thereto was added NaH (480 mg, 60%). The mixture was stirred at 0° C. for 10 minutes, and stirred at room temperature for one hour. Methyl 4-(bromomethyl)benzoate (2.50 g) was added to the mixture, and the mixture was stirred at room temperature for 2 hours. To the mixture was added ice water (50 mL), and extracted three times with ethyl acetate-toluene, and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=10/1→3/1) to give methyl 4-(1H-pyrazol-1-ylmethyl)benzoate (2.17 g, 92%). 1H NMR (CDCl3, 400 MHz) δ 8.00 (d, 2H, J=8.3 Hz), 7.57 (d, 1H, J=2.2 Hz), 7.42 (d, 1H, J=2.2 Hz), 7.23 (d, 2H, J=8.3 Hz), 6.31 (dd, 1H, J=2.2, 2.2 Hz), 5.38 (s, 2H), 3.90 (s, 3H).
References:
US2003/181496,2003,A1
