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

HRID 1059858

반응식

HRID 1059858 반응식
[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

참가 물질

5

반응물 3

HCID 798IndoleHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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): Rf 0.25 (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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c05fad6bc2fe420a80f89d0ccca908f0
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521659B2

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