反应详情

To a slurry of NaH (680 mg [60% dispersion in oil]) in THF (250 ml) at 0° C. was added methyl 3-[(2-bromo-5-methoxybenzoyl)amino]-4-methylbenzoate (5.36 g) portionwise. The reaction was stirred for 30 minutes at room temperature when allyl bromide (1.6 ml) was added dropwise and the solution was stirred for a further 20 hours at room temperature. The reaction mixture was quenched with water and then concentrated. The residue was dissolved in ethyl acetate and washed with water (×2), brine, dried (magnesium sulfate) and concentrated. The residue was purified by column chromatography on a silica column eluting using a gradient of iso-hexane to 50% ethyl acetate/iso-hexane to yield methyl 3-[allyl(2-bromo-5-methoxybenzoyl)amino]-4-methylbenzoate as a colourless oil (4.88 g); Mass Spectrum: M+H+ 417.

1. additionwas added dropwise
2. customThe reaction mixture was quenched with water
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in ethyl acetate
5. washwashed with water (×2), brine
6. dry with materialdried (magnesium sulfate)
7. concentrationconcentrated
8. customThe residue was purified by column chromatography on a silica column
9. washeluting