反应详情

To 7-bromo-6-ethoxy-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (Compound A-4, 1.05 g, 3.53 mmol) in THF (12 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1])-pyrimidinone (2 mL) at 0° C. was added a solution of methylmagnesium bromide (3M in diethylether (3.53 mL, 10.59 mmol). The reaction was allowed to warm up to room temperature and was stirred at 50° C. overnight. The reaction was quenched with ice water and extracted with diethylether. The organic layer was washed successively with water, brine, dried over Na2SO4, and concentrated in vacuo. The crude material was then dissolved in benzene (20 mL). After catalytic amount of p-toluenesulfonic acid was added, the reaction was stirred at reflux for 2 h. The solvent was removed in vacuo. The residue was purified by column chromatography (silica gel, 1% ethyl acetate in hexane) to afford the title compound as a pale yellow oil.

1. customThe reaction was quenched with ice water
2. extractionextracted with diethylether
3. washThe organic layer was washed successively with water, brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. dissolutionThe crude material was then dissolved in benzene (20 mL)
7. additionAfter catalytic amount of p-toluenesulfonic acid was added
8. stirringthe reaction was stirred
9. temperatureat reflux for 2 h
10. customThe solvent was removed in vacuo
11. customThe residue was purified by column chromatography (silica gel, 1% ethyl acetate in hexane)