Methyl acetoacetate → HCID 178490910, Verbindung

HRID 47610

Reaktionsgleichung

Reaktionsgleichung von HRID 47610
Cl.Cl.[CH3:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([CH2:9][NH:10][NH2:11])=[CH:7][CH:6]=1.C(N(CC)CC)C.[C:21](OC)(=[O:26])[CH2:22][C:23]([CH3:25])=O>C1(C)C=CC=CC=1>[CH3:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([CH2:9][N:10]2[C:21]([OH:26])=[CH:22][C:23]([CH3:25])=[N:11]2)=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 7757Methyl acetoacetateHCID 8471TriethylamineHCID 22747476(4-Methoxybenzyl)hydrazine dihydrochloride

Produkt 1

HCID 178490910HCID 178490910, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution containing 2.75 g of (4-methoxybenzyl)hydrazine dihydrochloride in 50 ml of toluene was treated with 1.7 ml of triethylamine at rt and then stirred for 5 min. The mixture was then treated with 1.32 ml of methyl acetoacetate and heated at 100° C. for 15 min. The solvent was evaporated under reduced pressure and then the residue partitioned between dichloromethane/10% citric acid and extracted three times. Combined extracts were washed with brine, then dried over anhydrous magnesium sulphate, filtered and evaporated to give a yellow solid. The solid was purified by flash chromatography on silica gel using methanol/dichloromethane (1:49) for the elution to give 2.3 g of 2-(4-methoxybenzyl)-5-methyl-2H-pyrazol-3-ol as a white solid. Mass spectrum (ES) m/z 219 [M+H]+.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between dichloromethane/10% citric acid
  3. extractionextracted three times
  4. washCombined extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a yellow solid
  9. customThe solid was purified by flash chromatography on silica gel
  10. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-5779c6194f914b70860d7ff1cb025ff6
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699887B2

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