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Hexane → 3-phenyl-5-(2-pyridylcarbonylmethyl)-N-methyl-isoxazole-4-carboxamide

HRID 461799
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 461799
[C:1]1([C:7]2[C:11]([C:12]([NH:14][CH3:15])=[O:13])=[C:10]([CH3:16])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34](OCC)=[O:35]>O1CCCC1>[C:1]1([C:7]2[C:11]([C:12]([NH:14][CH3:15])=[O:13])=[C:10]([CH2:16][C:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=3)=[O:35])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 17307Ethyl 2-pyridinecarboxylateHCID 4104650N,5-Dimethyl-3-phenyl-4-isoxazolecarboxamideHCID 178418339Butyllithium

Produkt 1

HCID 227620923-phenyl-5-(2-pyridylcarbonylmethyl)-N-methyl-isoxazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

A suspension of 28 g. (0.13 mole) of 3-phenyl-N,5-dimethyl- isoxazole-4-carboxamide and 330 milliliters of tetrahydrofuran is cooled to -65° C. and 180 milliliters of 1.6M n-butyllithium in hexane (0.288 mole) is added dropwise, maintaining the temperature between -60° and -70° C. After the addition is complete, the organic suspension is stirred for 11/2 hours at -60° to -70° C., and then 19.6 g. (0.13 mole) of ethyl picolinate in 196 ml. tetrahydrofuran is added drop-wise maintaining the temperature between -60° and -70° C. After addition is complete, the mixture is stirred 11/2 hours at -60° to -70° C. and then warmed to -30° C. and quenched by the addition of saturated ammonium chloride solution. The mixture is further diluted with tetrahydrofuran and the layers are separated. The tetrahydrofuran layer is washed twice with 50% brine, and once with brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The solid residue is triturated with ether and filtered to give 3-phenyl-5-(2-pyridylcarbonylmethyl)-N-methyl-isoxazole-4-carboxamide; m.p. 146° to 149° C.

Aufarbeitung

  1. additionA suspension of 28 g
  2. temperaturemaintaining the temperature between -60° and -70° C
  3. additionAfter the addition
  4. temperaturemaintaining the temperature between -60° and -70° C
  5. additionAfter addition
  6. stirringthe mixture is stirred 11/2 hours at -60° to -70° C.
  7. customquenched by the addition of saturated ammonium chloride solution
  8. additionThe mixture is further diluted with tetrahydrofuran
  9. customthe layers are separated
  10. washThe tetrahydrofuran layer is washed twice with 50% brine
  11. dry with materialonce with brine, dried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. customevaporated in vacuo
  14. customThe solid residue is triturated with ether
  15. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-26bba8c11854461080ea754256f163af
Quelldatensatz
uspto-grants-1977_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04064251

Notizen zur Reaktion

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