Triethylamine → 2-(1-Dodecynyl)thiophene

HRID 235179

反応式

HRID 235179 の反応式
I[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[CH:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)CC)C>[Cu]I.O1CCCC1>[C:7]([C:2]1[S:3][CH:4]=[CH:5][CH:6]=1)#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 189212-IodothiopheneHCID 698211-Dodecyne

生成物 1

HCID 183729932-(1-Dodecynyl)thiophene収率 739%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
55 °C

実験手順

To a solution of 2-iodothiophene (31.5 g), 1-dodecyne (2.5 g), triethylamine (105 ml), and tetrahydrofuran (100 ml) was added (bis)triphenylphosphine palladium(II)chloride (1.73 g) followed by copper(I)iodide (0.24 g). The reaction mixture was warmed to 55° C. and stirred for 7 hr. The solution was allowed to cool to room temperature and stirred overnight. The mixture was filtered, and the precipitate was washed with ethyl acetate. The filtrate was diluted with ethyl acetate and washed with water and brine. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was flash chromatographed over silica gel (elated with hexane). The appropriate fractions were collected and evaporated. The residue was distilled to afford 27.6 g (74%) of product, bp 145°-150° C. at 0.7 mm Hg.

後処理

  1. temperatureto cool to room temperature
  2. stirringstirred overnight
  3. filtrationThe mixture was filtered
  4. washthe precipitate was washed with ethyl acetate
  5. additionThe filtrate was diluted with ethyl acetate
  6. washwashed with water and brine
  7. customThe organic phase was separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated in vacuo
  11. customchromatographed over silica gel (elated with hexane)
  12. customThe appropriate fractions were collected
  13. customevaporated
  14. distillationThe residue was distilled

出典と根拠

ORDレコード
ord-a5c356321837494d8c050da15a5dc5c6
出典データセット
uspto-grants-1997_01
特許番号
US05597838

関連ノート

読み込み中…