Ethyl 4-bromobenzoate → Ethyl 4-(4-n-pentyloxyphenylethynyl)benzoate

HRID 351536

反応式

HRID 351536 の反応式
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH2:13]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[CH:26])=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH3:17]>C(N(CC)CC)C.N1C=CC=CC=1.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:13]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[C:26][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH3:17]

参加物

8

反応物 2

HCID 22043Ethyl 4-bromobenzoateHCID 27751191-Eth-1-ynyl-4-(pentyloxy)benzene

生成物 1

HCID 22713259Ethyl 4-(4-n-pentyloxyphenylethynyl)benzoate収率 35.2%

試薬・触媒・溶媒 5

HCID 11776Triphenylphosphine触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 1049Pyridine溶媒HCID 8471Triethylamine溶媒

反応条件

温度
80 °C

実験手順

To a suspension of ethyl 4-bromobenzoate (1.37 g), (4-n-pentyloxyphenyl)acetylene (565 mg), triphenylphosphine (16 mg) and copper(I) iodide (6 mg) in triethylamine (10 ml) and pyridine (4 ml) was added palladium(II) chloride bis(triphenylphosphine) (21 mg) and the reaction mixture was stirred for 24 hours at 80° C. After cooling, the precipitate was filtered off, and the filtrate was evaporated under reduced pressure. The residue was taken up to dichloromethane, and the solution was washed successively with 1N HCl, water, brine and dried over magnesium sulfate. The solvents were removed under reduced pressure and the residue was triturated with acetonitrile, collected by filtration and dried under reduced pressure to give ethyl 4-(4-n-pentyloxyphenylethynyl)benzoate (355 mg).

後処理

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. washthe solution was washed successively with 1N HCl, water, brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvents were removed under reduced pressure
  7. customthe residue was triturated with acetonitrile
  8. filtrationcollected by filtration
  9. customdried under reduced pressure

出典と根拠

ORDレコード
ord-75df36affa3b4e1c9e154e2606ab4cdf
出典データセット
uspto-grants-2004_06
特許番号
US06743776B2

関連ノート

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