Potassium Hydroxide → 2,4-Dimethyl-5-carboxy-1H-pyrrole-3-propanoic acid 5-ethyl ester

HRID 24330노트

반응식

HRID 24330 반응식
[CH3:1][C:2]1[NH:3][C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:5]([CH3:14])[C:6]=1[CH2:7][CH2:8][C:9]([O:11]CC)=[O:10].[OH-].[K+]>O.CO>[CH2:18]([O:17][C:15]([C:4]1[NH:3][C:2]([CH3:1])=[C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[C:5]=1[CH3:14])=[O:16])[CH3:19]

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 291761Ethyl 2,4-dimethyl-5-(ethoxycarbonyl)-3-pyrrolepropionate

생성물 1

HCID 1422052,4-Dimethyl-5-carboxy-1H-pyrrole-3-propanoic acid 5-ethyl ester수율 80.6%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매2회

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온도
70 °C

실험 절차

To a suspension of 10 g (38.9 mmol) ethyl 2,4-dimethyl-5-(ethoxycarbonyl)-3-pyrrolepropionate (commercially available) in a mixture of water (250 mL) and methanol (MeOH) (50 mL) was added 3.0 g of KOH in 50 mL of water. The mixture was stirred at 70° C. for 4 hr. The reaction mixture was cooled and the methanol was stripped from the mixture under vacuum. The remaining solution was filtered and the filtrate was then acidified with 6N hydrochloric acid to pH 3. The precipitate which formed was collected by filtration, washed with a 2:1 mixture of water and ethanol and dried under vacuum to give 7.5 g of 4-(2-carboxy-ethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester as a white solid.

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe remaining solution was filtered
  3. customThe precipitate which formed
  4. filtrationwas collected by filtration
  5. washwashed with a 2:1 mixture of water and ethanol
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-b83993ba834544a5b266a7678a49131a
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855730B2

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