Ethyl 3-(N,N-dimethylamino)acrylate → Ethyl 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylate

HRID 487620

Reaktionsgleichung

Reaktionsgleichung von HRID 487620
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([C:11]2[CH:19]=[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]3[N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CN(C)[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:5]1([C:11]2[C:19]([CH:22]=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]3[N:12]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

6

Edukt 4

HCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 156203422-Phenylpyrazolo[1,5-a]pyridine

Produkt 1

HCID 53784179Ethyl 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylateAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Aluminum chloride (298 mg) was added portionwise to a solution of 2-phenylpyrazolo[1,5-a]pyridine (145 mg) and ethyl 3-dimethylaminoacrylate (316 mg) in methylene chloride (2 ml) at 5° to 6° C. After being stirred at room temperature overnight, the reaction mixture was poured onto water (50 ml), neutralized with saturated aqueous sodium bicarbonate solution, and extracted with chloroform (50 ml×2). The extracts were washed with saturated sodium chloride aqueous solution (20 ml), dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel with a mixture of chloroform and n-hexane (1:1) as an eluent. The fractions containing the objective compound were combined and evaporated in vacuo to give ethyl 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylate (trans isomer) (189.4 mg).

Aufarbeitung

  1. additionthe reaction mixture was poured onto water (50 ml)
  2. extractionextracted with chloroform (50 ml×2)
  3. washThe extracts were washed with saturated sodium chloride aqueous solution (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel with a mixture of chloroform and n-hexane (1:1) as an eluent
  7. additionThe fractions containing the objective compound
  8. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ad4d292f8f0f4a0487636ab1377b8f59
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05296490

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