反応 #977656

反応方程式

2-methyl-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid ethyl ester

lithium aluminium hydride

NaOH

→

title compound

収率 48.0%

[2-Methyl-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol

収率 48.0%

溶媒

diethyl ether

diethyl ether

反応条件

後処理

1. 1
   温度at reflux for 12 h
2. 2
   ろ過The reaction mixture was filtered over celite, t-butyl methylether
3. 3
   workup.ADDITIONwas added
4. 4
   その他the layers were separated
5. 5
   抽出The aqueous layer was extracted one more time with t-butyl methylether
6. 6
   洗浄the combined organic layers were washed with ice water/brine 1/1
7. 7
   乾燥dried over sodium sulfate
8. 8
   その他Removal of the solvent under reduced pressure
9. 9
   その他gave a brown oil which
10. 10
    その他was purified by column chromatography (silica gel, heptane/AcOEt)

実験手順

A solution of 2-methyl-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid ethyl ester (200 mg, 0.5 mmol) in diethyl ether (3 ml) was added to a suspension of lithium aluminium hydride (40 mg, 1 mmol) in diethyl ether (6 ml) under an argon atmosphere at ambient temperature within 5 min. The mixture was stirred at reflux for 12 h, cooled to 0° C. and treated cautiously with ice water (6 ml) and 10% aqueous NaOH (3 ml). The reaction mixture was filtered over celite, t-butyl methylether was added and the layers were separated. The aqueous layer was extracted one more time with t-butyl methylether, the combined organic layers were washed with ice water/brine 1/1 and dried over sodium sulfate. Removal of the solvent under reduced pressure gave a brown oil which was purified by column chromatography (silica gel, heptane/AcOEt) to yield 80 mg (240 μmol, 45%) of the title compound as yellow crystals.

出典