Acetic Anhydride → 1-[1-(4-Ethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

HRID 2375369노트

반응식

HRID 2375369 반응식
[C:1](OC(=O)C)(=[O:3])[CH3:2].I.[CH3:9][C:10]1[N:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=2)[C:12]([CH3:15])=[CH:13][CH:14]=1>[OH-].[Na+]>[C:1]([C:13]1[CH:14]=[C:10]([CH3:9])[N:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=2)[C:12]=1[CH3:15])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 24841Hydrogen iodideHCID 8460412,5-dimethyl-1-(4-ethoxyphenyl)pyrrole

생성물 1

HCID 201096531-[1-(4-Ethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
100 °C

실험 절차

Acetic anhydride (8.5 mL, 89 mmol) and hydriodic acid (0.48 mL, 6.3 mmol) were added to 2,5-dimethyl-1-(4-ethoxyphenyl)pyrrole (8.0 g, 37 mmol) under nitrogen and the resulting mixture maintained at 100° C. overnight. After cooling to rt, the mixture was diluted with 1N NaOH (200 mL), extracted with EtOAc (2×200 mL), and the combined extracts washed with brine (200 mL), dried (MgSO4), filtered, concentrated in vacuo, and purified by flash chromatography on silica gel (15% EtOAc/hexanes) to give 3-acetyl-2,5-dimethyl-1-(4-ethoxyphenyl)pyrrole as a tan solid: 1H NM (CDCl3, 500 MHz) δ 7.08-7.04 (m, 2H), 6.99-6.96 (m, 2H), 6.30 (s, 1H), 4.08 (q, 2H), 2.41 (s, 3H), 2.29 (s, 3H), 1.97 (s, 3H), 1.45 (t, 3H); MS (ESI) 258 (M+H)+.

후처리

  1. temperatureAfter cooling to rt
  2. extractionextracted with EtOAc (2×200 mL)
  3. washthe combined extracts washed with brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel (15% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-11d5c72f262d4f8280fa31883157ecbd
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465730B2

반응 노트

불러오는 중…