Tributylamine → HCID 66691768、化合物

HRID 330821

反応式

HRID 330821 の反応式
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:2].[CH2:19]([O:21][CH:22]([O:25]CC)[CH:23]=[CH2:24])[CH3:20].C(N(CCCC)CCCC)CCC.CCOC(C)=O>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:19]([O:21][C:22](=[O:25])[CH2:23][CH2:24][C:15]1[CH:16]=[CH:17][C:12]([C:11]#[C:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)=[CH:13][CH:14]=1)[CH3:20]

参加物

8

反応物 4

HCID 7622TributylamineHCID 8857Ethyl AcetateHCID 624773,3-Diethoxy-1-propene2 回HCID 66691575HCID 66691575、化合物

生成物 1

HCID 66691768HCID 66691768、化合物

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To 1.80 g (5.17 mmol) 1-ethoxy-4-((4-iodophenyl)ethynyl)benzene (XII.1) in 24 mL DMF are added 2.36 mL (15.5 mmol) 3,3-diethoxy-propene, 3.69 mL (15.5 mmol) tributylamine, 1.44 g (5.17 mmol) tetrabutylammoniumchloride and 0.04 g (0.16 mmol) palladium(II)acetate under argon. The mixture is stirred at 120° C. for 12 h. After that time, 1.18 mL (7.76 mmol) 3,3-diethoxy-propene are added and the mixture is stirred at 120° C. for 5 d. After cooling, EtOAc is added and the mixture is washed with 1N potassium hydrogensulfate solution and water. The organic layer is dried over sodium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silica gel; PE:DCM 1:1) to yield the desired product.

後処理

  1. stirringthe mixture is stirred at 120° C. for 5 d
  2. temperatureAfter cooling
  3. washthe mixture is washed with 1N potassium hydrogensulfate solution and water
  4. dry with materialThe organic layer is dried over sodium sulphate
  5. customthe solvent is evaporated
  6. customThe residue is purified by column chromatography (silica gel; PE:DCM 1:1)

出典と根拠

ORDレコード
ord-caeaae0a8b5941e9b57e00af235f045f
出典データセット
uspto-grants-2014_11
特許番号
US08877754B2

関連ノート

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