Benzyl Bromide → 1-Benzyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 642220ノート

反応式

HRID 642220 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][NH:8][C:7]=1[CH3:11])=[O:5])[CH3:2].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][N:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]=1[CH3:11])=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 136747Ethyl 2-methyl-3-pyrrolecarboxylate

生成物 1

HCID 107289331-Benzyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester収率 58%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A mixture of 2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (6.05 g, 39.24 mmol), benzyl bromide (5.14 mL, 43.17 mmol) in DMF (50 mL) was cooled with an ice-water bath, then the solids of NaH (1.89 g, 47.09 mmol) were added in one portion, the mixture was stirred at 0° C. for 1.5 h, then quenched with saturated ammonium chloride aqueous solution, diluted with EtOAc, the organic phase was washed with water and saturated sodium chloride aqueous solution, respectively, dried over anhydrous sodium sulfate, filtered, concentrated, and the residue was purified with column chromatography to give the desired title product (5.537 g); 1H NMR (200 MHz, CDCl3): δ (ppm)=7.30 (m, 3H), 6.95 (m, 2H), 6.57 (d, 1H, J=3.0 Hz), 6.53 (d, 1H, J=3.0 Hz), 5.03 (s, 2H), 4.25 (q, 2H, J=7.0 Hz), 2.44 (s, 3H), 1.34 (t, 3H, J=7.0 Hz).

後処理

  1. temperaturewas cooled with an ice-water bath
  2. customquenched with saturated ammonium chloride aqueous solution
  3. additiondiluted with EtOAc
  4. washthe organic phase was washed with water and saturated sodium chloride aqueous solution
  5. dry with materialrespectively, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified with column chromatography

出典と根拠

ORDレコード
ord-dfff5fd8c99c47f596125d64d0cd8a11
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

反応ノート

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