2,2-Dimethyl-1,3-dioxane-4,6-dione → 2,2-DiMethyl-5-[(2,4,5-trifluorophenyl)acetyl]-1,3-dioxane-4,6-dione

HRID 221421

Reaktionsgleichung

Reaktionsgleichung von HRID 221421
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[F:11][C:12]1[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:13]=1[CH2:20][C:21](O)=[O:22].Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH:5]([C:21](=[O:22])[CH2:20][C:13]2[CH:14]=[C:15]([F:19])[C:16]([F:18])=[CH:17][C:12]=2[F:11])[C:4](=[O:9])[O:3]1

Komponenten

6

Edukt 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27779502,4,5-Trifluorophenylacetic acid

Produkt 1

HCID 497840752,2-DiMethyl-5-[(2,4,5-trifluorophenyl)acetyl]-1,3-dioxane-4,6-dioneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2,2-Dimethyl-[1,3]dioxane-4,6-dione (5.69 g, 39.5 mmol) was dissolved in 400 mL of dichloromethane under stirring, followed by addition of (2,4,5-trifluorophenyl)-acetic acid 1a (7.15 g, 37.6 mmol) and 4-dimethylaminopyridine (7.35 g, 60.2 mmol) in an ice-water bath. Then a suspension of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.28 g, 43.2 mmol) in 250 mL of dichloromethane was added dropwise slowly. After stirring at room temperature for 36 hours, the reaction mixture was washed with the solution of 5% potassium bisulfate (250 mL×7) and saturated brine (250 mL×2), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 2,2-dimethyl-5-[2-(2,4,5-trifluoro-phenyl)-acetyl]-[1,3]dioxane-4,6-dione 1b (11.4 g, yield 96%) as a white solid.

Aufarbeitung

  1. additionwas added dropwise slowly
  2. stirringAfter stirring at room temperature for 36 hours
  3. washthe reaction mixture was washed with the solution of 5% potassium bisulfate (250 mL×7) and saturated brine (250 mL×2)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-95593b41e190407bbe52c20bfa2f8c4d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207161B2

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