反応 #1005938

反応方程式

1-(4-chloro-phenyl)-3-((Z)-3-tributylstannanyl-but-2-enyloxy)-1H-pyrazole

iodine

→

1-(4-chlorophenyl)-3-[(Z)-3-iodobut-2-enoxy]pyrazole

溶媒

methylene chloride

反応条件

後処理

1. 1
   その他After removal of the solvents in vacuo the crude product
2. 2
   workup.DISSOLUTIONwas dissolved in 200 ml MTBE
3. 3
   workup.ADDITION100 ml 20% aqueous potassium fluoride solution have been added
4. 4
   workup.STIRRINGthe mixture was stirred for 2 h at ambient temperature
5. 5
   その他The aqueous layer was separated
6. 6
   抽出extracted with 20 ml methyl-tert.-butyl ether twice
7. 7
   洗浄The combined organic phases have been washed twice with 20 ml of water each,
8. 8
   乾燥dried with sodium sulfate
9. 9
   その他the solvents were removed in vacuo
10. 10
    その他The crude product (7.2 g) has been purified by chromatography on 50 g silica with methyl-tert.-butylether/hexane (1:20)

実験手順

To 10.0 g (18.6 mmol) 1-(4-chloro-phenyl)-3-((Z)-3-tributylstannanyl-but-2-enyloxy)-1H-pyrazole in 100 ml methylene chloride have been added 4.7 g (18.6 mmol) iodine at ambient temperature with stirring which was continued for 3 h. After removal of the solvents in vacuo the crude product was dissolved in 200 ml MTBE. 100 ml 20% aqueous potassium fluoride solution have been added and the mixture was stirred for 2 h at ambient temperature. The aqueous layer was separated and extracted with 20 ml methyl-tert.-butyl ether twice. The combined organic phases have been washed twice with 20 ml of water each, dried with sodium sulfate, and the solvents were removed in vacuo. The crude product (7.2 g) has been purified by chromatography on 50 g silica with methyl-tert.-butylether/hexane (1:20). Yield 5.9 g, melting point 75-77° C.

出典