反应详情

In a 100-mL three-neck flask were put 0.53 g (2.5 mmol) of 4-chlorobenzo[h]quinazoline, 52 mg (0.148 mmol) of tris(2,4-pentanedionato)iron(III) (abbreviation: Fe(acac)3), 25 mL of dehydrated tetrahydrofuran (THF), and 2.0 mL of 1-methyl-2-pyrrolidone (abbreviation: NMP), and the air in the flask was replaced with nitrogen. The flask was cooled with ice, 2.6 mL of isobutylmagnesium bromide solution (1 M in THF) (abbreviation: iBuMgBr) was added, and the mixture was stirred at room temperature for 16 hours. Then, 1 M hydrochloric acid was added, and an organic layer was subjected to extraction with ethyl acetate. The solution of the extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. After washing, anhydrous magnesium sulfate was added to the organic layer for drying. The resulting mixture was subjected to gravity filtration, and the filtrate was concentrated to give a residue. The residue was purified by silica gel column chromatography. As the developing solvent, first, dichloromethane was used; then, a 10:1 dichloromethane-ethyl acetate mixed solvent was used. The resulting fraction was concentrated to give 0.14 g of an orange oily substance in a yield of 24%. Synthesis Scheme (b-1) of Step 1 is shown below.

1. customIn a 100-mL three-neck flask were put
2. additionwas added
3. extractionan organic layer was subjected to extraction with ethyl acetate
4. washThe solution of the extract was washed with a saturated aqueous solution of sodium hydrogen carbonate
5. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
6. washAfter washing
7. additionanhydrous magnesium sulfate was added to the organic layer
8. customfor drying
9. filtrationThe resulting mixture was subjected to gravity filtration
10. concentrationthe filtrate was concentrated
11. customto give a residue
12. customThe residue was purified by silica gel column chromatography
13. concentrationThe resulting fraction was concentrated
14. customto give 0.14 g of an orange oily substance in a yield of 24%
15. customSynthesis Scheme (b-1) of Step 1