反応 #366655

反応方程式

Magnesium

bromoethane

1-bromo-2-(2-tetrahydropyranyloxymethyl)benzene

N-methoxy-3, N-dimethyl-5-isoxazolcarboxamide

→

2-(2-tetrahydropyranyloxymethyl)phenyl 3-methylisoxazol-5-yl ketone

収率 67.9%

溶媒

water

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at −60° C. to room temperature for 1 hour
2. 2
   抽出the mixture was extracted with ether (200 ml)
3. 3
   乾燥The extract was dried over anhydrous magnesium sulfate
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他The residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

実験手順

Magnesium (0.73 g, 0.03 mol) and bromoethane (0.2 ml) were added to a mixture of 1-bromo-2-(2-tetrahydropyranyloxymethyl)benzene (5.42 g, 0.02 mol) and THF (50 ml) under an atmosphere of nitrogen gas, and the resulting mixture was stirred at 50 to 60° C. for 1 hour to prepare Grignard reagent. The Grignard reagent was added dropwise to a mixture of N-methoxy-3, N-dimethyl-5-isoxazolcarboxamide (3.40 g, 0.02 mol) and THF (40 ml). The mixture was stirred at −60° C. to room temperature for 1 hour, water (200 ml) was added, and the mixture was extracted with ether (200 ml). The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(2-tetrahydropyranyloxymethyl)phenyl 3-methylisoxazol-5-yl ketone (4.09 g, yield: 67.9%) as a colorless oil.

出典