L-Proline → 4-(2-Ethyl-4-hydroxyphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

HRID 512579

Reaktionsgleichung

Reaktionsgleichung von HRID 512579
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]2=[O:19])=[C:4]([CH2:20][CH3:21])[CH:3]=1.N1CCC[C@H]1C(O)=[O:25]>[OH-].[Na+].C(OCC)(=O)C.Cl.[Cu]I>[CH2:20]([C:4]1[CH:3]=[C:2]([OH:25])[CH:7]=[CH:6][C:5]=1[CH:8]1[C:9](=[O:19])[C:10]([CH3:18])([CH3:17])[O:11][C:12]([CH3:16])([CH3:15])[C:13]1=[O:14])[CH3:21]

Komponenten

7

Edukt 2

HCID 145742L-ProlineHCID 497653874-(4-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

Produkt 1

HCID 666775534-(2-Ethyl-4-hydroxyphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 4-(4-bromo-2-ethylphenyl)-2,2,6,6,-tetramethylpyran-3,5-dione (1.00 g, 2.8 mmol), copper(I) iodide (0.108 g, 0.57 mmol), and L-proline (0.033 g, 0.28 mmol) in 1M aqueous sodium hydroxide solution (8.8 ml) is heated at 200° C. under microwave irradiation, until the reaction is judged to be complete by LCMS. The mixture is cooled to room temperature, diluted with ethyl acetate and 2 M aqueous hydrochloric acid and filtered through a plug of diatomaceous earth, washing with ethyl acetate. The organic phase is collected, and the aqueous phase is extracted with ethyl acetate. The organic solutions are combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-(2-ethyl-4-hydroxyphenyl)-2,2,6,6-tetramethylpyran-3,5-dione.

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationfiltered through a plug of diatomaceous earth
  3. washwashing with ethyl acetate
  4. customThe organic phase is collected
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated under reduced pressure
  10. customThe residue is purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-01f191bebdcf4d66844f7f3b3162164b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102642B2

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