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

HRID 1662049노트

반응식

HRID 1662049 반응식
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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f0ddd5cf5ba747468d5da868cece4134
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030489B2

반응 노트

불러오는 중…