Tributylamine → HCID 66691768, 화합물

HRID 330821

반응식

HRID 330821 반응식
[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]

참가 물질

8

반응물 4

HCID 7622TributylamineHCID 8857Ethyl AcetateHCID 624773,3-Diethoxy-1-propene2회HCID 66691575HCID 66691575, 화합물

생성물 1

HCID 66691768HCID 66691768, 화합물

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-caeaae0a8b5941e9b57e00af235f045f
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877754B2

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