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

반응식

HRID 1073918 반응식
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]

참가 물질

7

반응물 2

HCID 27790724-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrileHCID 19895696HCID 19895696, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 24290Palladium Chloride촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8021Diethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8614dd0ab5c04322b44c419a256b1f64
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04971982

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