Imidazole → 3-(2-Iodoethyl)-7-methoxy-1-benzofuran

HRID 1178812ノート

反応式

HRID 1178812 の反応式
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH2:13]O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:34]I.N1C=CN=C1>C1COCC1>[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH2:13][I:34])[C:7]=2[CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 226629353-(2-Hydroxyethyl)-7-methoxybenzofuran

生成物 1

HCID 236144473-(2-Iodoethyl)-7-methoxy-1-benzofuran

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 2-(7-methoxy-1-benzofuran-3-yl)ethanol (960 mg, 5 mmol) in anhydrous THF (50 ml), triphenylphosphine (1.572 g, 6 mmol), iodine (1.518 g, 6 mmol) and imidazole (408 mg, 6 mmol) were added at room temperature. The reaction mixture was stirred at room temperature for 4 hrs and quenched with water. The mixture was then extracted with chloroform, washed well with 5% Na2S2O3 solution and the organic layer dried over anhydrous MgSO4. It was then filtered and concentrated. The residue was purified by silica-gel column chromatography by eluting it with 30% ethyl acetate:hexane. The product, 2-(7-methoxy-1-benzofuran-3-yl)ethyl iodide, was obtained as a brown liquid. Yield: 1.3 g (86%); (M+H): 302.

後処理

  1. customquenched with water
  2. extractionThe mixture was then extracted with chloroform
  3. washwashed well with 5% Na2S2O3 solution
  4. dry with materialthe organic layer dried over anhydrous MgSO4
  5. filtrationIt was then filtered
  6. concentrationconcentrated
  7. customThe residue was purified by silica-gel column chromatography
  8. washby eluting it with 30% ethyl acetate

出典と根拠

ORDレコード
ord-f46e7d2007a84caf9d6ae20234802835
出典データセット
uspto-grants-2007_10
特許番号
US07276603B2

反応ノート

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