反応 #55871

反応方程式

α-trichloromethyl-2-thiophenemethanol

methanol

potassium hydroxide

methanol

Thiophenol

→

α-phenylthio-2-thiopheneacetic acid

収率 76.0%

反応条件

後処理

1. 1
   workup.WAITAfter 10 min.
2. 2
   温度the mixture was gradually heated up
3. 3
   温度was heated
4. 4
   温度under reflux for 2 hr
5. 5
   その他after removal of most of the solvent
6. 6
   workup.DISTILLATIONby distillation under a reduced pressure, diethylether
7. 7
   workup.ADDITIONwas added
8. 8
   その他The ether layer was separated
9. 9
   洗浄washed with water
10. 10
    乾燥dried with anhydrous magnesium sulfate
11. 11
    ろ過After filtration
12. 12
    濃縮the filtrate was concentrated under a reduced pressure
13. 13
    その他the residue was purified by silica gel column chromatography (ethyl acetate: n-hexane=1:4)

実験手順

Under an argon atmosphere, potassium hydroxide (1.12 g, 20 mmol) was dissolved in methanol (10 ml). Thiophenol (0.6 g, 5.45 mmol) was added to this solution with stirring and under water cooling. After 10 min., a solution of α-trichloromethyl-2-thiophenemethanol (1.16 g, 5 mmol) in methanol (3 ml) was added. After 10 min., the mixture was gradually heated up and was heated under reflux for 2 hr. with vigorous stirring. After cooling to room temperature and after removal of most of the solvent by distillation under a reduced pressure, diethylether was added and the mixture was decomposed with dilute hydrochloric acid. The ether layer was separated, washed with water, and dried with anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate: n-hexane=1:4) to give 940 mg of α-phenylthio-2-thiopheneacetic acid as a viscous oil.

出典