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

HRID 490328ノート

反応式

HRID 490328 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21892291Methanol tetrahydrofuran water溶媒

反応条件

温度
75 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-affd9ab03d1a41febbd17463c5b02f33
出典データセット
uspto-grants-2009_05
特許番号
US07528156B2

反応ノート

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