Reaktion #366655

Reaktionsgleichung

Magnesium

bromoethane

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

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

→

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

Ausbeute 67.9%

Lösungsmittel

water

THF

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle