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

HRID 642220노트

반응식

HRID 642220 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dfff5fd8c99c47f596125d64d0cd8a11
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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