Indole → Indol-1-yl-acetic acid ethyl ester

HRID 1268072

反応式

HRID 1268072 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(#N)C>[N:1]1([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

参加物

5

反応物 3

HCID 798IndoleHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

生成物 1

HCID 967684Indol-1-yl-acetic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Under an atmosphere of nitrogen, a solution of indole (15.0 g, 128 mmol) in dry acetonitrile (300 mL, 0.4 M) was treated with sodium hydride (95%, 3.69 g, 153 mmol) and stirred for 30 min. Ethyl bromoacetate (17.0 mL, 153 mmol) was added in a dropwise manner over 10 min and the solution was stirred at room temperature for 16 h. After concentrating under reduced pressure, the resulting residue was dissolved in ethyl acetate and washed with sat'd. aq. NaCl. The organic extracts were dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography (50% ethyl acetate in heptane): Rf0.25 (40% ethyl acetate in heptane) 1H NMR (DMSO-d6, 300 MHz) δ 7.53 (d, J=6.3 Hz, 1H), 7.38-7.31 (m, 2H), 7.11 (br t, J=7.2 Hz, 1H), 7.02 (br t, J=7.2 Hz, 1H), 6.45-6.43 (m, 1H), 5.10 (s, 2H), 4.12 (q, J=7.2 Hz, 2H), 1.19 (t, J=7.2 Hz, 3H).

後処理

  1. stirringthe solution was stirred at room temperature for 16 h
  2. concentrationAfter concentrating under reduced pressure
  3. dissolutionthe resulting residue was dissolved in ethyl acetate
  4. washwashed with sat'd
  5. dry with materialThe organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography (50% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-c013744753c7460c98b898eeec29ffbe
出典データセット
uspto-grants-2003_04
特許番号
US06555568B1

関連ノート

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