反応 #417507

反応方程式

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

hydrazine hydrate

acetic acid

→

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

収率 96.5%

溶媒

ethanol

反応条件

後処理

1. 1
   workup.ADDITIONboth added via syringe
2. 2
   workup.ADDITIONUpon completion of addition the reaction mixture
3. 3
   温度was heated
4. 4
   温度at reflux for 7 hours
5. 5
   workup.STIRRINGwas stirred for 18 hours
6. 6
   濃縮The reaction mixture was concentrated under reduced pressure
7. 7
   workup.STIRRINGthe residue was stirred with diethyl ether and water
8. 8
   その他The mixture was placed in a separatory funnel
9. 9
   その他the layers were separated
10. 10
    洗浄The organic layer was washed with aqueous 10% sodium hydroxide solution, two portions of water
11. 11
    濃縮The organic layer was concentrated under reduced pressure

実験手順

A mixture of 1.6 grams (0.004 mole) of (4-trifluoromethylsulfonyloxyphenyl)(2,3-dihydro-2,2-dimethylbenzofuran-5-yl) ketone in 75 mL of ethanol was stirred, and 0.6 mL (0.0121 mole) of hydrazine hydrate followed by 0.5 mL of acetic acid were both added via syringe. Upon completion of addition the reaction mixture was heated at reflux for 7 hours and then was allowed to cool to ambient temperature where it was stirred for 18 hours. The reaction mixture was concentrated under reduced pressure, and the residue was stirred with diethyl ether and water. The mixture was placed in a separatory funnel, and the layers were separated. The organic layer was washed with aqueous 10% sodium hydroxide solution, two portions of water, and with a saturated, aqueous solution of sodium chloride. The organic layer was concentrated under reduced pressure to yield 1.6 grams of (4-trifluoromethylsulfonyloxyphenyl)(2,3-dihydro-2,2-dimethylbenzofuran-5-yl) ketone hydrazone as an oil. The nmr spectrum was consistent with the proposed structure.

出典