4-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile → Benzyl 2-[3-(4-cyanophenoxy)-3-methyl-1-butyn-1-yl]pyridine-5-carboxylate

HRID 1073918ノート

反応式

HRID 1073918 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:4][N:3]=1.[CH3:18][C:19]([CH3:31])([O:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1)[C:20]#[CH:21]>C(NCC)C.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:27]([C:26]1[CH:29]=[CH:30][C:23]([O:22][C:19]([CH3:18])([CH3:31])[C:20]#[C:21][C:2]2[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])=[CH:4][N:3]=2)=[CH:24][CH:25]=1)#[N:28]

参加物

7

反応物 2

HCID 27790724-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrileHCID 19895696HCID 19895696、化合物

生成物 1

HCID 19895702Benzyl 2-[3-(4-cyanophenoxy)-3-methyl-1-butyn-1-yl]pyridine-5-carboxylate収率 74.9%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 24290Palladium Chloride触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8021Diethylamine溶媒

実験手順

12.2 g of benzyl 2-iodopyridine-5-carboxylate and 5.64 g of 4-(1,1-dimethyl-2-propynyloxy)benzonitrile were stirred with 32 mg of copper(I) iodide, 162 mg of triphenylphosphine and 180 mg of palladium(II) chloride in 280 ml of diethylamine at room temperature for 7 days under a nitrogen atmosphere. The mixture was evaporated and the residue was taken up in ethyl acetate and water. The organic phase was separated, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. There were obtained 9.04 g of benzyl 2-[3-(4-cyanophenoxy)-3-methyl-1-butyn-1-yl]pyridine-5-carboxylate which was used without further purification.

後処理

  1. customThe mixture was evaporated
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washfor the elution

出典と根拠

ORDレコード
ord-8614dd0ab5c04322b44c419a256b1f64
出典データセット
uspto-grants-1990_11
特許番号
US04971982

反応ノート

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