反応 #51596

反応方程式

NaH

6-hydroxy-2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methylpyridine

NaH

(E)-1,3-dichloropropene

→

title compound

収率 52.3%

(E)-2-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methyl-6-(3-chloroprop-2-enyloxy)pyridine

収率 52.3%

溶媒

pentane ethyl acetate

acetonitrile

DMF

反応条件

後処理

1. 1
   workup.STIRRINGAfter stirring for 60 h at ambient temperature
2. 2
   ろ過filtered through a bed of silica gel
3. 3
   洗浄The filtrate is washed with water
4. 4
   乾燥The organic layer is dried with anhydrous magnesium sulfate
5. 5
   ろ過filtered
6. 6
   その他evaporated in vacuo
7. 7
   その他Purification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v)

実験手順

A mixture of 6-hydroxy-2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methylpyridine (0.9 g, 3.3 mmol) and NaH (60% in oil, 0.16 g, 4 mmol) in acetonitrile (20 ml) and DMF (1 ml) is stirred for 10 min at ambient temperature and (E)-1,3-dichloropropene (0.4 g, 3.6 mmol) is added. After stirring for 60 h at ambient temperature, the remaining NaH is deactivated and the resulting mixture is diluted with pentane/ethyl acetate (by volume ration 1/1) and filtered through a bed of silica gel. The filtrate is washed with water. The organic layer is dried with anhydrous magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v) yields the title compound (0.6 g, 52% yield) as an colorless oil.

出典