Reaction #1702072

Reaction equation

5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl-N-methoxy-N-methylamide

ammonium chloride

PhBr

benzene bromide

diethyl ether

benzene bromide

magnesium

iodine

→

5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl phenyl ketone

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureAfter cooling down to room temperature
2. 2
   workup.STIRRINGwhich was then stirred at room temperature for 22 hours
3. 3
   Extractionextracted by ethyl acetate
4. 4
   WashThe organic layer was washed by water
5. 5
   Dryinga saturated sodium hydrogen carbonate aq. solution and a saturated saline solution, dried over magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe crude product was purified by silica gel chromatography

Procedure

The synthesis process is as set forth in the chemical reaction formula below. The PhBr in the reaction path stands for benzene bromide. To benzene bromide (1.17 g, 7.50 mmol) were added anhydrous tetrahydrofuran (10 mL), magnesium (911 mg, 37.5 mol) and iodine, followed by stirring at 80° C. After cooling down to room temperature, the mixture was added to 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl-N-methoxy-N-methylamide (J) (55.0 mg, 0.200 mmol) dissolved in anhydrous diethyl ether (2 mL), which was then stirred at room temperature for 22 hours. The reaction solution was poured into a saturated ammonium chloride aq. solution and extracted by ethyl acetate. The organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (2/1) as an elution solvent. The yield was 14.9 mg (25%).

Source