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

HRID 1626

反応式

HRID 1626 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fd2ce529eb5e4230a968d9b7a9207cfc
出典データセット
uspto-grants-1998_03
特許番号
US05726195

関連ノート

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