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

HRID 2375369ノート

反応式

HRID 2375369 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

反応条件

温度
100 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-11d5c72f262d4f8280fa31883157ecbd
出典データセット
uspto-grants-2008_12
特許番号
US07465730B2

反応ノート

読み込み中…