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Sodium Hydroxide → 5-(Phenylmethyl)-1H-pyrrole-2-carboxylic acid

HRID 1457450
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HRID 1457450 반응식
[CH2:1]([C:8]1[NH:12][C:11]([C:13]([O:15]CC)=[O:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([C:8]1[NH:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 14449694HCID 14449694, 화합물

생성물 1

HCID 184690125-(Phenylmethyl)-1H-pyrrole-2-carboxylic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of Ethyl 5-benzylpyrrole-2-carboxylate (0.7 g, 3.05 mmol; Elder et al., Synthetic Communications, 19, 763-767 (1989)), ethanol (20 ml) and 1M sodium hydroxide (9.2 ml, 9.2 mmol) was stirred and heated under reflux for 3 h. The major part of the ethanol was removed and the remaining liquid was diluted with water, washed with ether, cooled in ice and acidified with concentrated hydrochloric acid. The mixture was extracted with ether. The combined extracts were washed with brine, dried (Na2SO4) and concentrated to afford 0.567 g (92%) of an off white solid: mp. 130°-134° C.; 1H NMR(CDCl3) δ 8.87 (1H, brs), 7.37-6.95 (5H, m), 6.97 (1H, m), 6.07 (1H, m), 4.00 (2H, s).

후처리

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. customThe major part of the ethanol was removed
  4. additionthe remaining liquid was diluted with water
  5. washwashed with ether
  6. temperaturecooled in ice
  7. extractionThe mixture was extracted with ether
  8. washThe combined extracts were washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customto afford 0.567 g (92%) of an off white solid

출처 및 근거

ORD 기록
ord-cead61097b514bf6ae7dc2bdc90be888
출처 데이터셋
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05847135

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