Hydrochloric Acid → HCID 11384598、化合物

HRID 1869288ノート

反応式

HRID 1869288 の反応式
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]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 80271Tri-o-tolylphosphineHCID 53544532-ButenaMide, N,N-diethyl-, (E)-HCID 113143551-[4-Bromo-7-(1-phenylethoxy)benzofuran-2-yl]ethanone2 回

生成物 1

HCID 11384598HCID 11384598、化合物収率 43.6%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8471Triethylamine溶媒

反応条件

温度
84 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-19e8944c48184a8eb325e2d9537b6e81
出典データセット
uspto-grants-2009_12
特許番号
US07638540B2

反応ノート

読み込み中…