反応 #417506

反応方程式

4-(trifluoromethylsulfonyloxy)-4'-(2-methyl-2-propenoxy)benzophenone

magnesium chloride

→

(4-trifluoromethylsulfonyloxyphenyl)(2,3-dihydro-2,2-dimethylbenzofuran-5-yl) ketone

収率 77.2%

溶媒

diethyl ether

反応条件

後処理

1. 1
   ろ過The mixture was filtered through diatomaceous earth
2. 2
   その他the filtrate was placed in a separatory funnel
3. 3
   洗浄washed with two portions of aqueous 0.5 N sodium hydroxide, three portions of water, and one portion of a saturated, aqueous, sodium chloride solution
4. 4
   乾燥The organic layer was dried with sodium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮The filtrate was concentrated under reduced pressure to a residue
7. 7
   その他The residue was purified
8. 8
   洗浄Elution
9. 9
   濃縮concentrated under reduced pressure

実験手順

A mixture of 4.4 grams (0.011 mole) of 4-(trifluoromethylsulfonyloxy)-4'-(2-methyl-2-propenoxy)benzophenone and 0.05 gram (0.0005 mole) of magnesium chloride was stirred under a nitrogen atmosphere at 170°-175° C. for 20 hours. The reaction mixture was cooled to ambient temperature, and diethyl ether was added. The mixture was filtered through diatomaceous earth, and the filtrate was placed in a separatory funnel and washed with two portions of aqueous 0.5 N sodium hydroxide, three portions of water, and one portion of a saturated, aqueous, sodium chloride solution. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified by centrifically accelerated, radial thin layer chromatography. Elution was accomplished using 3:1 methylene chloride:hexane. The appropriate fractions were combined and concentrated under reduced pressure to yield 1.7 grams of (4-trifluoromethylsulfonyloxyphenyl)(2,3-dihydro-2,2-dimethylbenzofuran-5-yl) ketone. The nmr spectrum was consistent with the proposed structure.

出典