反応 #360564

反応方程式

ethyl 2,2-difluoro-3-(4-methoxyphenyl)propanoate

aluminum chloride

1-octanethiol

→

title compound

収率 56.0%

ethyl 2,2-difluoro-3-(4-hydroxyphenyl)propanoate

収率 56.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他described in Synthesis, vol. 13
2. 2
   workup.STIRRINGthe mixture was stirred for 30 min
3. 3
   その他The organic layer was separated
4. 4
   洗浄washed with saturated brine
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他The residue was purified by silica gel column chromatography (8%-60% ethyl acetate/hexane)

実験手順

To a solution of ethyl 2,2-difluoro-3-(4-methoxyphenyl)propanoate (1.72 g, 7.05 mmol) synthesized according to the method described in Synthesis, vol. 13, pp. 1917-1924 (2000) and aluminum chloride (2.82 g, 21.2 mmol) in dichloromethane (50 mL) was added dropwise 1-octanethiol (2.06 g, 14.1 mmol) and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into ice water and the mixture was stirred for 30 min. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (8%-60% ethyl acetate/hexane) to give the title compound (0.90 g, yield 56%) as a colorless oil.

出典