反応 #69562

反応方程式

1-Decanol

sodium

3-bromo-thiophene

→

3-Decyloxythiophene

溶媒

water

反応条件

後処理

1. 1
   その他After complete disappearance of sodium, the residual alcohol was removed in vacuum
2. 2
   workup.DISSOLUTIONthe remaining solid was dissolved in 20˜30 ml DMF
3. 3
   抽出extracted with ether three times
4. 4
   濃縮The filtrate was concentrated in vacuo
5. 5
   その他the yellow oily residue was chromatographed on a silica column

実験手順

3-Decyloxythiophene was synthesized as follows. 1-Decanol (0.51 mol, 80.27 g) was added dropwise to 3.5 g (0.15 mol) of sodium metal. After complete disappearance of sodium, the residual alcohol was removed in vacuum and the remaining solid was dissolved in 20˜30 ml DMF. After the solution was heated to 110° C., 12.2 g (0.075 mol) of 3-bromo-thiophene and 1.0 g (0.00053 mol) of copper (I) iodide were added. After 16 hrs of stirring at 110° C., the mixture was poured into water and extracted with ether three times. The filtrate was concentrated in vacuo and the yellow oily residue was chromatographed on a silica column using hexane as the eluent to yield 15.5 g of yellow liquid (86% yield). Mw=240.4. Element Anal. Calcd for C14H24SO: C, 69.94; H, 10.06; 0, 6.66; S, 13.34. Found: C, 69.90; H, 10.00; 0, 6.64; S, 13.30.

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