反応 #595184

反応方程式

2-bromo-1,3-dimethylbenzene

4-hydroxyindan-1-one

potassium carbonate

pyridine

→

title compound

収率 2.2%

4-(2,6-dimethylphenoxy)indan-1-one

収率 2.2%

溶媒

o-xylene

methanol

toluene

反応条件

後処理

1. 1
   温度After cooling the reaction mixture
2. 2
   ろ過The insoluble material was filtered off
3. 3
   濃縮the filtrate was concentrated
4. 4
   workup.ADDITIONWater was added to the residue
5. 5
   抽出the mixture was extracted with ethyl acetate
6. 6
   洗浄The organic layer was washed with 1 M hydrochloric acid, water and saturated brine
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   濃縮concentrated under reduced pressure
9. 9
   workup.ADDITIONChloroform was added to the residue
10. 10
    ろ過the insoluble material was filtered off
11. 11
    その他the filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=90/10-hexane/ethyl acetate=0/100)

実験手順

A mixture of 2-bromo-1,3-dimethylbenzene (15.0 g, 81.1 mmol), 4-hydroxyindan-1-one (10.0 g, 67.5 mmol), copper(II) oxide (9.13 g, 114 mmol), potassium carbonate (18.7 g, 135 mmol), pyridine (200 mL) and o-xylene (100 mL) was stirred under a nitrogen atmosphere at 130° C. for 18 hr. After cooling the reaction mixture, a mixed solvent of toluene and methanol was added. The insoluble material was filtered off, and the filtrate was concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1 M hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Chloroform was added to the residue, the insoluble material was filtered off and the filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=90/10-hexane/ethyl acetate=0/100) to give the title compound (0.373 g, yield 2%) as a yellow oil.

出典