تفاعل #42487

معادلة التفاعل

methyl 6-[(methylsulfonyl)methyl]nicotinate

lithium hydroxide

→

title compound

المردود 93.2%

6-[(Methylsulfonyl)methyl]nicotinic acid

المردود 93.2%

المذيبات

tetrahydrofuran methanol water

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated under reduced pressure
2. 2
   أخرىThe residue was partitioned between water (10 mL) and chloroform (10 mL)
3. 3
   استخلاصextracted with 3:1 chloroform/2-propanol (3×30 mL)
4. 4
   تجفيفThe combined organic layers were dried (sodium sulfate)
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated under reduced pressure

الإجراء التجريبي

To a stirred solution of methyl 6-[(methylsulfonyl)methyl]nicotinate (800 mg) in 1:1.1 tetrahydrofuran/methanol/water (30 mL) was added lithium hydroxide (440 mg). The mixture was stirred at room temperature for 1 h, and concentrated under reduced pressure. The residue was partitioned between water (10 mL) and chloroform (10 mL). The aqueous layer was acidified to pH 4 with 1 N hydrochloric acid and extracted with 3:1 chloroform/2-propanol (3×30 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide 700 mg of the title compound: 1H NMR (300 MHz, CD3OD) δ 9.07, 8.33, 7.65, 4.77, 3.06.

المصدر