反応 #2286282

反応方程式

[4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-3,5-dimethyl-phenyl]-acetic acid methyl ester

[4-(6-Chloro-5-isopropyl-pyridazin-3-yloxy)-3,5-dimethyl-phenyl]-acetic acid methyl ester

sodium hydroxide

→

[4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-3,5-dimethyl-phenyl]-acetic acid

[4-(6-Chloro-5-isopropyl-pyridazin-3-yloxy)-3,5-dimethyl-phenyl]-acetic acid

溶媒

methanol

反応条件

後処理

1. 1
   その他at room temperature
2. 2
   濃縮At this time, the reaction mixture was concentrated under vacuum
3. 3
   workup.ADDITIONThe resulting solid was diluted with water (200 mL)
4. 4
   抽出extracted with ethyl acetate (200 mL)
5. 5
   workup.ADDITIONThe water layer was acidified to pH=4 by the addition of a 1N aqueous hydrochloric acid solution
6. 6
   抽出was extracted with ethyl acetate (2×200 mL)
7. 7
   洗浄washed with a saturated aqueous sodium chloride solution
8. 8
   乾燥dried with magnesium sulfate
9. 9
   ろ過filtered
10. 10
    濃縮concentrated under vacuum
11. 11
    その他to afford a solid
12. 12
    その他The solid was dried overnight under high vacuum

実験手順

A solution of [4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-3,5-dimethyl-phenyl]-acetic acid methyl ester (8a) (1.66 g, 4.75 mmol, contains a minor amount of isomer) in methanol (50 mL) at room temperature was treated dropwise with a 1N aqueous sodium hydroxide solution (9.5 mL, 9.50 mmol). The reaction was stirred at room temperature for 24 h. At this time, the reaction mixture was concentrated under vacuum. The resulting solid was diluted with water (200 mL) and extracted with ethyl acetate (200 mL). The ethyl acetate layer was discarded. The water layer was acidified to pH=4 by the addition of a 1N aqueous hydrochloric acid solution and was extracted with ethyl acetate (2×200 mL). The organic layers were combined, washed with a saturated aqueous sodium chloride solution, dried with magnesium sulfate, filtered and concentrated under vacuum to afford a solid. The solid was dried overnight under high vacuum to afford [4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-3,5-dimethyl-phenyl]-acetic acid (9a) (1.58 g, 100%, contains a minor amount of isomer) as an off-white solid; EI(+)-HRMS m/z calcd for C17H19ClN2O3 (M+) 334.1084, found 334.1083. Molecular Weight=334.8056; Exact Mass=334.1084

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