Ethyl 3-(4-pyridyl)-3-oxopropionate → 1,1'-(2-Hydroxy-5-methyl-1,3-phenylene)di(ethan-1-one)

HRID 1817789

Reaktionsgleichung

Reaktionsgleichung von HRID 1817789
O=[C:2](C1C=CN=CC=1)CC(OCC)=O.[OH:15][C:16]1[C:21]([CH2:22][O:23]C)=[CH:20][C:19]([CH3:25])=[CH:18][C:17]=1[C:26](=[O:28])[CH3:27].CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C.Cl[Pd]Cl>[C:26]([C:17]1[C:16]([OH:15])=[C:21]([C:22](=[O:23])[CH3:2])[CH:20]=[C:19]([CH3:25])[CH:18]=1)(=[O:28])[CH3:27]

Komponenten

7

Edukt 3

HCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 132292322'-Hydroxy-5'-methyl-3'-methoxymethylacetophenoneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 23050491,1'-(2-Hydroxy-5-methyl-1,3-phenylene)di(ethan-1-one)

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24290Palladium ChlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of a bromo derivative 1 (324 mg, 1 mmol), (R)-(+)-α-methylbenzylamine 2 (122 mg, 1 mmol), potassium t-butoxide (225 mg, 2 mmol) and PdCl2 (dppf) (35 mg, 0.05 mmol) in THF was stirred at refluxing temperature for 20 hours over a nitrogen atmosphere. The reaction mixture was cooled and diluted with ethyl acetate. The organic layer was washed with water, brine and dried over Na2SO4. The ethyl acetate layers was concentrated in vacuo and the residue was subjected to column chromatography (silica gel, ethylacetate) to give the required product 3. 1H NMR (300 MHz, CDCl3), δ 8.78 (br s, 2H), 8.21 (s, 1H), 7.92 (d, J=5.9 Hz, 2H), 7.4-7.26 (m, 5H), 6.90 (s, 1H), 6.50 (d, J=5.5 Hz, 1H, —NH), 6.27 (s, 1H), 4.60 (m, 1H), 2.23 (s, 3H), 1.71 (d, J=6.9 Hz, 311). MS (m/z)=357.13 (m+1).

Aufarbeitung

  1. temperatureat refluxing temperature for 20 hours over a nitrogen atmosphere
  2. temperatureThe reaction mixture was cooled
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe ethyl acetate layers was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b80831f730a94cec96ee5db0dbba60da
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598377B2

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