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Hydrochloric Acid → 3-(2,2-dimethyl4-oxo4H-1,3-benzodioxin-5-yl)-benzoic acid, ethyl ester

HRID 1583103
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1583103
[CH3:1][C:2]1([CH3:21])[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11](OS(C(F)(F)F)(=O)=O)[C:5]=2[C:4](=[O:20])[O:3]1.[CH2:22]([O:24][C:25]([C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1)=[O:26])[CH3:23].C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]1([CH3:21])[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([C:31]3[CH:32]=[C:27]([CH:28]=[CH:29][CH:30]=3)[C:25]([O:24][CH2:22][CH3:23])=[O:26])[C:5]=2[C:4](=[O:20])[O:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 3249312(3-Ethoxycarbonylphenyl)boronic acidHCID 108927482,2-Dimethyl-4-oxo-4H-benzo[D][1,3]dioxin-5-YL trifluoromethanesulfonate

Produkt 1

HCID 207287193-(2,2-dimethyl4-oxo4H-1,3-benzodioxin-5-yl)-benzoic acid, ethyl esterAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2,2-dimethyl-5-trifluoromethane-sulfonyloxy-4H-1,3-benzodioxin-4-one (2.0 g, 5.8 mmol), 3-ethoxycarbonylphenylboronic acid (1.34 g, 6.9 mmol) and anhydrous K2CO3 powder (2.61 g, 18.9 mmol) in DMF (30 mL) was added tetrakis(triphenylphosphine)palladium (0.202 g, 0.175 mmol). The mixture was heated at reflux for 2 h. The reaction mixture was allowed to cool to room temperature (“rt”) and 1 N HCl (25 mL) was added. The mixture was extracted with EtOAc (3×25 mL). The combined extracts were washed with water and brine, then dried over MgSO4, filtered, and concentrated. The crude material was purified by flash chromatography (1:15 EtOAc/hexanes) to afford 3-(2,2-dimethyl4-oxo4H-1,3-benzodioxin-5-yl)-benzoic acid, ethyl ester (1.2 g, 63%) as a white solid: 1H NMR (CDCl3) δ1.39 (t, J=7.1 Hz, 3H), 1.80 (s, 6H), 4.39 (q, J=7.0 Hz, 2H), 7.01 (d, J=8.0 Hz, 2H), 7.47-7.57 (m, 3H), 8.00 (t, J=1.5 Hz, 1H) 8.07 (dt, J=7.5, 1.5 Hz, 1H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. additionwas added
  4. extractionThe mixture was extracted with EtOAc (3×25 mL)
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by flash chromatography (1:15 EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3935e5feb05e49059d70b81c03116796
Quelldatensatz
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06740777B2

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