Potassium Hydroxide → 2,5-Diethynylthiophene

HRID 1443022

반응식

HRID 1443022 반응식
IC1SC(I)=CC=1.C[Si](C#C)(C)C.C[Si]([C:18]#[C:19][C:20]1[S:21][C:22]([C:25]#[C:26][Si](C)(C)C)=[CH:23][CH:24]=1)(C)C.[OH-].[K+]>CO.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.O.C(N(CC)CC)C>[C:19]([C:20]1[S:21][C:22]([C:25]#[CH:26])=[CH:23][CH:24]=1)#[CH:18]

참가 물질

9

반응물 4

HCID 14797Potassium HydroxideHCID 66111TrimethylsilylacetyleneHCID 693682,5-DiiodothiopheneHCID 127020072,5-Bis[(trimethylsilyl)ethynyl]thiophene

생성물 1

HCID 113440402,5-Diethynylthiophene수율 72%

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 887Methanol용매HCID 962Water용매HCID 8471Triethylamine용매

실험 절차

To a 250 mL flask were added 2.5 g of 2,5-diiodothiophene (7.44 mmol), 100 mg of Cul, and 220 mg of Pd(Ph3P)2Cl2 under nitrogen. Then 100 mL of triethylamine (TEA) and 5.0 mL of trimethylsilylacetylene (3.40 g, 35 mmol) were injected. The reaction mixture was allowed to stir at room temperature for 12 hours. The precipitate was removed by filtration and the solvent of the filtrate was evaporated. The crude intermediate, i.e. 2,5-bis(trimethylsilylethynyl)thiophene, was purified by column chromatography and thus hydrolysed with 3 g KOH (53.6 mmol) in 70 mL methanol for 2 hours. The solution was poured into a large amount of water, and extracted with diethyl ether twice. The resultant solution was washed with water three times, dried over magnesium sulphate, and then the solvent was removed under reduced pressure to give 2,5-diethynylthiophene as a pale yellow liquid (0.71 g, 72%).

후처리

  1. customThe precipitate was removed by filtration
  2. customthe solvent of the filtrate was evaporated
  3. extractionextracted with diethyl ether twice
  4. washThe resultant solution was washed with water three times
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-5e5347f295cc447d854dddb9e4f2546a
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659353B2

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