ethyl 5-hydroxymethyl-1,4-dimethyl-1H-pyrrole-2-carboxylate → 1,4,5-trimethyl-1H-pyrrole-2-carboxylic acid

HRID 1662049ノート

反応式

HRID 1662049 の反応式
O[CH2:2][C:3]1[N:7]([CH3:8])[C:6]([C:9]([O:11]CC)=[O:10])=[CH:5][C:4]=1[CH3:14]>[C].[Pd].C(O)C>[CH3:8][N:7]1[C:3]([CH3:2])=[C:4]([CH3:14])[CH:5]=[C:6]1[C:9]([OH:11])=[O:10]

参加物

4

反応物 1

HCID 59454025ethyl 5-hydroxymethyl-1,4-dimethyl-1H-pyrrole-2-carboxylate

生成物 1

HCID 594538791,4,5-trimethyl-1H-pyrrole-2-carboxylic acid収率 46.2%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒

実験手順

A mixture of ethyl 5-hydroxymethyl-1,4-dimethyl-1H-pyrrole-2-carboxylate (2.2 g), ethanol (15 ml), and palladium-carbon (2.2 g) was stirred at room temperature for 2 hours under a hydrogen atmosphere of 3 atmospheres. The insolubles of the reaction mixture were separated by filtration through Celite and the filtrate was concentrated to about 10 ml under reduced pressure. THF (10 ml) was added to the residue, and a 1 M aqueous sodium hydroxide solution (20 ml) was further added at room temperature, followed by stirring at room temperature for 13 days. The reaction mixture was washed with diethyl ether, and 1 M hydrochloric acid (20 ml) was added to the aqueous layer under ice-cooling. The solid precipitated was collected by filtration and washed with water to obtain 1,4,5-trimethyl-1H-pyrrole-2-carboxylic acid (0.79 g).

後処理

  1. customThe insolubles of the reaction mixture were separated by filtration through Celite
  2. concentrationthe filtrate was concentrated to about 10 ml under reduced pressure
  3. additionTHF (10 ml) was added to the residue
  4. additiona 1 M aqueous sodium hydroxide solution (20 ml) was further added at room temperature
  5. stirringby stirring at room temperature for 13 days
  6. washThe reaction mixture was washed with diethyl ether, and 1 M hydrochloric acid (20 ml)
  7. additionwas added to the aqueous layer under ice-
  8. temperaturecooling
  9. customThe solid precipitated
  10. filtrationwas collected by filtration
  11. washwashed with water

出典と根拠

ORDレコード
ord-f0ddd5cf5ba747468d5da868cece4134
出典データセット
uspto-grants-2011_10
特許番号
US08030489B2

反応ノート

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