Ethyl Acetate → 2-(5-Ethylthiophen-2-yl)-4-methoxybenzo(b)furan

HRID 460608ノート

反応式

HRID 460608 の反応式
[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([Sn](C)(C)C)[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Br[C:17]1[S:18][C:19]([CH2:22][CH3:23])=[CH:20][CH:21]=1.C(OCC)(=O)C>C1COCC1>[CH2:22]([C:19]1[S:18][C:17]([C:9]2[O:8][C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=3[CH:10]=2)=[CH:21][CH:20]=1)[CH3:23]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 227291122-Bromo-5-ethylthiopheneHCID 227291264-Methoxy-2-(trimethylstannyl)benzo(b)furan

生成物 1

HCID 227293132-(5-Ethylthiophen-2-yl)-4-methoxybenzo(b)furan収率 41.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-methoxy-2-(trimethylstannyl)benzo(b)furan (3.00 g) and 2-bromo-5-ethylthiophene (1.84 g) in THF (25 ml) was added bistriphenylphosphinepalladium dichloride (224 mg), and the mixture was stirred with refluxing overnight. After cooling, ethyl acetate was added to the reaction mixture and the mixture was filtered through celite. The filtrate was washed with water and saturated brine, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (1.04 g) as a yellow oil.

後処理

  1. temperaturewith refluxing overnight
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through celite
  4. washThe filtrate was washed with water and saturated brine
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-8a43020c355d4e4da451e3168d6d65ce
出典データセット
uspto-grants-2007_03
特許番号
US07196199B2

反応ノート

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