反応 #683111

反応方程式

triphenylphosphine

iodine

imidazole

(4-(6-fluoropyridin-3-yl)tetrahydro-2H-pyran-4-yl)methanol

→

2-fluoro-5-(4-(iodomethyl)tetrahydro-2H-pyran-4-yl)pyridine

収率 60.6%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   温度The reaction mixture was heated to 60° C. in an oil bath for 48 h
2. 2
   ろ過Solid was filtered off
3. 3
   その他the filtrate was purified by flash column chromatography on silicagel (ISCO)
4. 4
   洗浄eluting with 0-80% ethyl acetate in heptane
5. 5
   その他to give

実験手順

To an ice cooled solution of triphenylphosphine (983 mg, 3.75 mmol), iodine (952 mg, 3.75 mmol) in dichloromethane (20 mL) was added imidazole (278 mg, 4.09 mmol). The solution was stirred at ambient temperature for 1 h, followed by the addition of (4-(6-fluoropyridin-3-yl)tetrahydro-2H-pyran-4-yl)methanol (360 mg, 1.70 mmol) in 10 mL dichloromethane. The reaction mixture was heated to 60° C. in an oil bath for 48 h. Solid was filtered off, the filtrate was purified by flash column chromatography on silicagel (ISCO) eluting with 0-80% ethyl acetate in heptane to give to give 2-fluoro-5-(4-(iodomethyl)tetrahydro-2H-pyran-4-yl)pyridine (330 mg, 1.03 mmol, 60.3% yield) as light yellow color oil. LCMS (m/z): 322 (MH+), 0.77 min.

出典