Diethyl 2-(ethoxymethylidene)-3-oxobutanedioate → Triethyl 1,6-dihydro-6-oxo-2,3,5-pyridinetricarboxylate

HRID 54182

반응식

HRID 54182 반응식
C([CH:3]([C:7]([NH2:9])=[O:8])[C:4]([O-:6])=[O:5])C.C(O[CH:13]=[C:14]([C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])C.[C:27]([O-])(=O)[CH3:28].[Na+]>C(O)C>[CH2:25]([O:24][C:22]([C:20]1[NH:9][C:7](=[O:8])[C:3]([C:4]([O:6][CH2:27][CH3:28])=[O:5])=[CH:13][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:23])[CH3:26]

참가 물질

5

반응물 3

HCID 40590Diethyl 2-(ethoxymethylidene)-3-oxobutanedioateHCID 517045Sodium AcetateHCID 21894451Ethylmalonamate

생성물 1

HCID 19958207Triethyl 1,6-dihydro-6-oxo-2,3,5-pyridinetricarboxylate수율 80.3%

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
0 °C

실험 절차

A solution of ethylmalonamate (23.6 g, 0.18 mol) in absolute ethanol (300 mL) is added to a stirred solution of diethyl ethoxymethyleneoxalacetate (44.0 g, 0.18 mol) in ethanol (200 mL) at 0° C., followed by the addition, of solid sodium acetate (14.72 g, 0.18 mol). After stirring for ten minutes at 0° C., the mixture is heated to reflux and stirred for 13.5 hours. After cooling, the ethanol is removed under vacuum, and the residue diluted with water and acidified to pH 2 with concentrated hydrochloric acid. The aqueous solution is extracted with methylene chloride (2×200 mL) and the organic layer washed with 300 mL saturated sodium chloride, then dried over anhydrous magnesium sulfate and concentrated in vacuum to give 45.0 g of the title product as an orange oil.

후처리

  1. temperaturethe mixture is heated
  2. temperatureto reflux
  3. stirringstirred for 13.5 hours
  4. temperatureAfter cooling
  5. customthe ethanol is removed under vacuum
  6. additionthe residue diluted with water
  7. extractionThe aqueous solution is extracted with methylene chloride (2×200 mL)
  8. washthe organic layer washed with 300 mL saturated sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-e115c8113c62468c9cc104c1ac9af4d3
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622913

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