Triethylamine → 2-(1-Dodecynyl)thiophene

HRID 235179

반응식

HRID 235179 반응식
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]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 189212-IodothiopheneHCID 698211-Dodecyne

생성물 1

HCID 183729932-(1-Dodecynyl)thiophene수율 739%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
55 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a5c356321837494d8c050da15a5dc5c6
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597838

연결된 노트

불러오는 중…