تفاعل #412174

معادلة التفاعل

pentafluoropyridine

methyl thioglycolate

cesium carbonate

2-benzyloxy-5-cyanophenol

cesium carbonate

KOH

→

4-benzyloxy-3-[(4-(methoxycarbonylmethyl)thio-3,5,6-trifluoropyridin-2-yl)oxy]benzonitrile

المردود 56.2%

المذيبات

acetonitrile

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was then cooled to ambient temperature
2. 2
   أخرىThe organic layer was separated
3. 3
   غسيلwashed further with 150 mL of 0.5 M aqueous KOH solution
4. 4
   تجفيفbrine (150 mL), dried over MgSO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىto afford a yellow oil
8. 8
   أخرىPurification by flash chromatography on silica gel

الإجراء التجريبي

To a solution of pentafluoropyridine (1.9 g, 11.2 mmol) in acetonitrile (25 mL) at 0° C. was added methyl thioglycolate (1.0 mL, 11.2 mmol) and cesium carbonate (4.4 g, 13.5 mmol). The resultant mixture was allowed to warm slowly to ambient temperature and stirred for 16 hours. To the mixture was added 2-benzyloxy-5-cyanophenol (2.6 g, 11.5 mmol) and cesium carbonate (4.4 g, 13.5 mmol). The resultant mixture was stirred at 40° C. for 16 hours. The mixture was then cooled to ambient temperature and poured into 150 mL of 0.5 M aqueous KOH solution and 150 mL of ethyl acetate. The organic layer was separated and washed further with 150 mL of 0.5 M aqueous KOH solution, then brine (150 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford a yellow oil. Purification by flash chromatography on silica gel afforded 2.9 g (56% yield) of 4-benzyloxy-3-[(4-(methoxycarbonylmethyl)thio-3,5,6-trifluoropyridin-2-yl)oxy]benzonitrile, a compound of formula (E), as a pale yellow oil: NMR (CDCl3) 7.5-7.0 (m, 8), 5.1 (s, 2), 3.8 (s, 2), 3.7 (s, 3) ppm.

المصدر