Ethyl bromoacetate → Ethyl 4-Methoxyindole-3-acetate

HRID 51467

反応式

HRID 51467 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.C([Li])CCC.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>O1CCCC1.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][NH:7]2

参加物

7

反応物 3

HCID 7748Ethyl bromoacetateHCID 1383634-Methoxy-1H-indoleHCID 178418339Butyllithium

生成物 1

HCID 91078263Ethyl 4-Methoxyindole-3-acetate

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2.94 gm (20 mmol) of 4-methoxyindole in 150 ml of tetrahydrofuran was added slowly 13 ml of n-butyl lithium (1.6M in hexane; 20 mmol) followed by the slow addition of 20 ml of zinc chloride (1.0M in ethyl ether; 20 mmol) at 0-5° C. The cooling bath was removed and the solution stirred for 2 hours and then treated with 2.1 ml (25 mmol) of ethyl bromoacetate for 19 hours, diluted with ethyl acetate, washed with water, washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a gradient hexane/10-50% ethyl ether to give starting material (40%) and then product, 2.3 gm, 50%, as an oil. 1H NMR (CDCl3) δ: 1.25 (t, 3H), 3.85 (s, 3H), 3.90 (s, 2H), 4.10 (q, 2H), 6.45 (d, 1H), 6.90 (d, 1H), 6.95 (s, 1H), 7.05 (t, 1H), 8.00 (br s, 1H).

後処理

  1. customThe cooling bath was removed
  2. washwashed with water
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with a gradient hexane/10-50% ethyl ether
  7. customto give

出典と根拠

ORDレコード
ord-c1d2dc2209614685a7c4ac39f3fb5372
出典データセット
uspto-grants-2004_03
特許番号
US06713645B1

関連ノート

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