Hydrochloric Acid → HCID 11384598, 화합물

HRID 1869288노트

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HRID 1869288 반응식
Br[C:2]1[C:7]2[CH:8]=[C:9]([C:11](=[O:13])[CH3:12])[O:10][C:6]=2[C:5]([O:14][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])=[CH:4][CH:3]=1.[CH2:23]([N:25]([CH2:31][CH3:32])[C:26](=[O:30])/[CH:27]=[CH:28]/[CH3:29])[CH3:24].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([C:9]1[O:10][C:6]2[C:5]([O:14][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[CH:4][CH:3]=[C:2](/[C:28](/[CH3:29])=[CH:27]/[C:26]([N:25]([CH2:31][CH3:32])[CH2:23][CH3:24])=[O:30])[C:7]=2[CH:8]=1)(=[O:13])[CH3:12]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 80271Tri-o-tolylphosphineHCID 53544532-ButenaMide, N,N-diethyl-, (E)-HCID 113143551-[4-Bromo-7-(1-phenylethoxy)benzofuran-2-yl]ethanone2회

생성물 1

HCID 11384598HCID 11384598, 화합물수율 43.6%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8471Triethylamine용매

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온도
84 °C

실험 절차

1-[4-Bromo-7-(1-phenylethoxy)benzofuran-2-yl]ethanone (compound 3) (1.0 g, 2.79 mmol) and (E)-N,N-diethyl-2-butenamide (0.47 g, 3.35 mmol) were dissolved in triethylamine (10 ml), and the inside of the system was replaced by nitrogen gas. Palladium acetate (0.031 g, 0.14 mmol) and tri-o-tolylphosphine (0.085 g, 0.28 mmol) were added and the mixture was stirred with heating at 78-90° C. for 16 hr. After confirmation of the completion of the reaction by TLC, 5% HCl aqueous solution was added and the mixture was extracted with ethyl acetate. The mixture was washed with saturated brine, dried over MgSO4, and the solvent was evaporated to give a brown oil. Purification by silica gel column chromatography (hexane:acetone=5:1) was performed to give (E)-3-[2-acetyl-7-(1-phenylethoxy)benzofuran-4-yl]-N,N-diethyl-2-butenamide (0.51 g, yield 43.6%) as a pale-yellow crystal.

후처리

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe mixture was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. customthe solvent was evaporated
  6. customto give a brown oil
  7. customPurification by silica gel column chromatography (hexane:acetone=5:1)

출처 및 근거

ORD 기록
ord-19e8944c48184a8eb325e2d9537b6e81
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638540B2

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