反応 #975142

反応方程式

heptafluoropropyltrifluorovinyl ether

dimethyl 5-hydroxyisophthalate

Potassium t-butoxide

→

dimethyl 5-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy)isophthalate

溶媒

Tetrahydrofuran

反応条件

後処理

1. 1
   その他equipped with a stirring bar
2. 2
   workup.ADDITION(PE) addition funnel
3. 3
   その他resulted
4. 4
   その他resulting in a heterogeneous mixture
5. 5
   その他to form a reaction mixture
6. 6
   workup.STIRRINGto stir at room temperature for ˜24 hours
7. 7
   その他The reaction was quenched by the addition for 80 mL of 10% HCl to the reaction flask
8. 8
   その他to form a reaction material
9. 9
   濃縮The resulting material was concentrated at reduced pressure
10. 10
    workup.DISSOLUTIONThe material was then dissolved in dichloromethane (˜150 mL)
11. 11
    洗浄washed with 10% HCl (2×100 mL)
12. 12
    その他with water (˜100 mL) to form an organic phase
13. 13
    乾燥The separated organic phase was then dried over anhydrous sodium sulfate
14. 14
    ろ過The sodium sulfate was then filtered off
15. 15
    workup.ADDITIONthe resulting material containing a crude product
16. 16
    濃縮was concentrated at reduced pressure
17. 17
    その他The crude product was purified by column chromatography

実験手順

In a dry box, dimethyl 5-hydroxyisophthalate (63.0 g, 0.300 mol) was added to an oven-dried multiple neck reaction flask equipped with a stirring bar and a pressure equaling (PE) addition funnel. Tetrahydrofuran (THF, 1500 mL) was then added to the reaction flask, and the reaction mixture was stirred until a homogeneous solution resulted. Potassium t-butoxide (9.24 g, 0.0825 mol) was added to the reaction mixture, resulting in a heterogeneous mixture. Via the PE funnel, heptafluoropropyltrifluorovinyl ether (199.2 g, 0.075 mol) was added to the reaction flask to form a reaction mixture. The reaction mixture was allowed to stir at room temperature for ˜24 hours. The reaction was quenched by the addition for 80 mL of 10% HCl to the reaction flask to form a reaction material. The resulting material was concentrated at reduced pressure. The material was then dissolved in dichloromethane (˜150 mL) and then washed with 10% HCl (2×100 mL) and then with water (˜100 mL) to form an organic phase and an aqueous phase. The separated organic phase was then dried over anhydrous sodium sulfate. The sodium sulfate was then filtered off and the resulting material containing a crude product was concentrated at reduced pressure. The crude product was purified by column chromatography resulting in 100.87 g (70.63%) yield of the desired material, dimethyl 5-(1,1,2-trifluoro-2-(perfluoropropoxy)ethoxy)isophthalate.

出典