反応 #562988

反応方程式

6-oxabicyclo[3.1.0]hexane

5-bromo-1,2,3-trifluorobenzene

magnesium

→

(1S,2R)-2-(3,4,5-trifluorophenyl)cyclopentanol

収率 79.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.ADDITIONAfter the addition
2. 2
   温度the reaction mixture was heated
3. 3
   温度at reflux for 2 h
4. 4
   workup.ADDITIONwere added dropwise
5. 5
   その他The reaction mixture was quenched by the addition of a solution of ammonium chloride
6. 6
   workup.ADDITIONEther was added
7. 7
   その他the organic layer was collected
8. 8
   乾燥dried (Na2SO4)
9. 9
   濃縮concentrated
10. 10
    その他The crude product was purified by column chromatography on silica gel

実験手順

To a suspension of magnesium (2.88 g, 118 mmol) in THF (110 mL) was slowly added 5-bromo-1,2,3-trifluorobenzene (25 g, 118 mmol). After the addition, the reaction mixture was heated at reflux for 2 h. To this reaction mixture, copper (I) iodide (1.506 g, 7.91 mmol) and 6-oxabicyclo[3.1.0]hexane (9.93 g, 118 mmol) dissolved in THF (20 mL) were added dropwise. The reaction mixture warmed upon the addition of the epoxide. The reaction was stirred at rt for 2 h at rt. The reaction mixture was quenched by the addition of a solution of ammonium chloride. Ether was added and the organic layer was collected, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography on silica gel to give (1S,2R)-2-(3,4,5-trifluorophenyl)cyclopentanol (20.2 g, 93 mmol, 79% yield).

出典