Diisopropylamine → (Furan-2-ylethynyl)trimethylsilane

HRID 705002

반응식

HRID 705002 반응식
Br[C:2]1[O:3][CH:4]=[CH:5][CH:6]=1.C(NC(C)C)(C)C.C1COCC1.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.O>[O:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19]

참가 물질

8

반응물 4

HCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 66111TrimethylsilylacetyleneHCID 2776190Furan, 2-bromo-

생성물 1

HCID 11217431(Furan-2-ylethynyl)trimethylsilane수율 35.84%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

실험 절차

A mixture of 2-bromofuran (500 mg, 3.402 mmol), Pd(PPh3)2Cl2 (75.69 mg, 0.10784 mmol), CuI (40.17 mg, 0.2109 mmol) and diisopropylamine (0.89 ml, 6.395 mmol) in tetrahydrofuaran (THF) (4 ml) was degassed thoroughly with argon, and trimethylsilyl acetylene (0.648 ml, 4.694 mmol) was added at room temperature. After stirring the reaction mixture for 16 hours at room temperature, it was poured into water and extracted with dichloromethane. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate and the solvent was evaporated. The crude material was purified by column chromatography (100-200 mesh silica gel) using hexane as eluent to yield the desired (furan-2-ylethynyl)trimethylsilane (200 mg, 1.21 mmol, yield 35.84%).

후처리

  1. additionwas added at room temperature
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe crude material was purified by column chromatography (100-200 mesh silica gel)

출처 및 근거

ORD 기록
ord-8c0ad605730944dabba5b4e065da2eb3
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173401B2

연결된 노트

불러오는 중…