Triethylamine → 4-[(5-Nitro-furan-2-yl)-ethynyl]benzonitrile

HRID 1626

반응식

HRID 1626 반응식
Br[C:2]1[O:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][CH:6]=1.C(N(CC)CC)C.[C:17]([C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1)#[CH:18]>C(#N)C.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>[N+:7]([C:4]1[O:3][C:2]([C:18]#[C:17][C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)=[CH:6][CH:5]=1)([O-:9])=[O:8]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 2335822-Bromo-5-nitrofuranHCID 45472454-Ethynylbenzonitrile

생성물 1

HCID 196919514-[(5-Nitro-furan-2-yl)-ethynyl]benzonitrile

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

To a solution of 2-bromo-5-nitrofuran (1.65 g) and triethylamine (34 ml) in anhydrous acetonitrile (55 ml) under nitrogen was added bis(triphenylphosphine)palladium dichloride (130 mg) and cuprous iodide (35 mg). 4-Ethynylbenzonitrile (1.09 g) was added and the reaction mixture was stirred under nitrogen overnight. The mixture was evaporated to dryness and the residue was dissolved in dichloromethane (200 ml), dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography (ethyl acetate/hexane 1:10) and triturated with ethyl acetate/hexane (1:3) to give 4-[(5-nitro-2-furyl)-ethynyl]benzonitrile.

후처리

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in dichloromethane (200 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/hexane 1:10)
  7. customtriturated with ethyl acetate/hexane (1:3)

출처 및 근거

ORD 기록
ord-fd2ce529eb5e4230a968d9b7a9207cfc
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726195

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