Ethanol → 6-(4-Chloro-phenyl)-5-cyclopropylmethoxy-pyridine-2-carboxylic acid
반응식
C(Cl)(=[O:3])C.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=C(C#N)[CH:15]=[CH:14][C:13]=2[O:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)=[CH:8][CH:7]=1.[CH2:25]([OH:27])[CH3:26]>>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[C:26]([C:25]([OH:3])=[O:27])[CH:15]=[CH:14][C:13]=2[O:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)=[CH:8][CH:7]=1참가 물질
4
반응 조건
- 온도
- 90 °C
실험 절차
8.27 g acetylchloride was added dropwise to 120 mL ethanol at 0° C. After 5 minutes, 6 g 6-(4-chloro-phenyl)-5-cyclopropylmethoxy-pyridine-2-carbonitrile was added at 0° C. The reaction mixture was stirred at 90° C. over 20 h. The reaction mixture was partitioned between water and ethyl acetate; then extracted. The organic phase was washed with brine; then dried over MgSO4. The crude product was stirred at room temperature in tetrahydrofuran:water 45:20. 1.77 g lithium hydroxide was added. The reaction mixture was stirred at 80° C. over 7 hours. The reaction mixture was added over acetic acid and extracted with dichloromethane. The organic phase was washed with water; then dried over MgSO4 and purified by chromatography on silica gel with a gradient of heptane to heptane:ethyl acetate 2:1 to yield 4.50 g (70.31%) of the title compound as light yellow solid, MS 304.1 (M+H)+.