Ethylene Glycol → 2,4-Dimethyl-3-carboxy-ethylpyrrole

HRID 2357710노트

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HRID 2357710 반응식
C(OC([C:6]1[NH:7][C:8]([CH3:18])=[C:9]([CH2:12][CH2:13][C:14]([O:16]C)=[O:15])[C:10]=1[CH3:11])=O)C.[OH-:19].[K+].Cl.[CH2:22]([OH:25])[CH2:23]O>O>[CH3:18][C:8]1[NH:7][CH:6]=[C:10]([CH3:11])[C:9]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15].[CH3:13][CH2:12][CH2:9][C:8]1[NH:7][CH:6]=[C:10]([CH3:11])[C:23]=1[C:22]([OH:25])=[O:19]

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 291754Ethyl 4-(3-methoxy-3-oxopropyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate

생성물 2

HCID 15125193-(2,4-dimethyl-1H-pyrrol-3-yl)propanoic AcidHCID 684626212,4-Dimethyl-3-carboxy-ethylpyrrole수율 72%

시약·촉매·용매 1

HCID 962Water용매2회

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온도
190 °C

실험 절차

2-(2-thienyl)pyrrole was prepared according to Kruse C. G. et al, Heterocycles 26 (1985) 3141 and formylated yielding 2-formyl-5-(2-thienyl)pyrrole according to Bullock E. et al. J. Chem. Soc. (1963) 2326 2,4-dimethyl-3-carboxyethylpyrrole was prepared as follows: 2-ethoxycarbonyl-3,5-dimethyl-4-methoxycarbonylethylpyrrole (1.5 g, 5.9 mmol) and potassium hydroxide (6.6 g) were dissolved in ethyleneglycol (50 ml). The reaction mixture was refluxed (190° C.) for 3 h under nitrogen atmosphere. Water (10 ml) was added and the mixture was refluxed for an additional 2 h. The cooled reaction mixture was diluted with water (200 ml), acidified with concentrated hydrochloric acid and extracted with diethylether. The organic extracts were pooled, dried with sodium sulphate and evaporated to dryness. The product was purified with column chromatography using silica as a stationary phase and dichloromethane:methanol (10:1, v:v) as an eluent. Fractions containing the product were pooled and evaporated to dryness yielding 720 mg (72%) of 2,4-dimethyl-3-carboxy-ethylpyrrole.

후처리

  1. temperaturethe mixture was refluxed for an additional 2 h
  2. customThe cooled reaction mixture
  3. extractionextracted with diethylether
  4. dry with materialdried with sodium sulphate
  5. customevaporated to dryness
  6. customThe product was purified with column chromatography
  7. additionFractions containing the product
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-34083cf7e4394fb3aaf8f264914e5418
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07763439B2

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