1-Decanol → 3-Decyloxythiophene

HRID 41284

反応式

HRID 41284 の反応式
[CH2:1]([OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Na].Br[C:14]1[CH:18]=[CH:17][S:16][CH:15]=1>[Cu]I.O>[CH2:1]([O:11][C:14]1[CH:18]=[CH:17][S:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

参加物

6

反応物 3

HCID 81741-DecanolHCID 133833-BromothiopheneHCID 5360545Sodium

生成物 1

HCID 197606903-Decyloxythiophene

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒

反応条件

温度
110 °C

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.

後処理

  1. customAfter complete disappearance of sodium, the residual alcohol was removed in vacuum
  2. dissolutionthe remaining solid was dissolved in 20˜30 ml DMF
  3. extractionextracted with ether three times
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe yellow oily residue was chromatographed on a silica column

出典と根拠

ORDレコード
ord-4e17e7d239a34bc080fa141765d91d78
出典データセット
uspto-grants-2013_09
特許番号
US08530594B2

関連ノート

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