Sodium Hydroxide → 3,5-dimethyl-1H-pyrrole-2-carboxylic acid

HRID 490328

반응식

HRID 490328 반응식
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[C:8]([O:10]CC)=[O:9].[OH-].[Na+]>C1COCC1.O.CO.O>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[C:8]([OH:10])=[O:9]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 1374771H-Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl ester

생성물 1

HCID 27764683,5-dimethyl-1H-pyrrole-2-carboxylic acid수율 90%

시약·촉매·용매 2

HCID 962Water용매HCID 21892291Methanol tetrahydrofuran water용매

반응 조건

온도
75 °C

실험 절차

To a solution of ethyl 3,5-dimethyl-2-pyrrolecarboxylate (Aldrich) (504 mg, 3 mmol) in THF/H2O/MeOH (5:1:1, 30 ml) was added NaOH (480 mg, 12 mmol) in H2O (12 ml). The mixture was stirred at 75° C. overnight. The homogeneous mixture was washed with ether. To the aqueous layer was added a saturated aqueous KHSO4 solution until the pH was about 3. The solution was then extracted with dichloromethane. The extracts were dried over MgSO4 and evaporated. The residue was purified on silica (ethylacetate/methanol 90/10) to give the title compound (375 mg, 90%).

후처리

  1. washThe homogeneous mixture was washed with ether
  2. additionTo the aqueous layer was added a saturated aqueous KHSO4 solution until the pH was about 3
  3. extractionThe solution was then extracted with dichloromethane
  4. dry with materialThe extracts were dried over MgSO4
  5. customevaporated
  6. customThe residue was purified on silica (ethylacetate/methanol 90/10)

출처 및 근거

ORD 기록
ord-affd9ab03d1a41febbd17463c5b02f33
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528156B2

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