Potassium Phosphate, Tribasic → (E)-4-Methyl-5-(prop-1-en-1-yl)isobenzofuran-1(3H)-one

HRID 1848413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848413
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[B-](F)(F)(F)/[CH:10]=[CH:11]/[CH3:12].[K+].FC(F)(F)S(O[C:23]1[C:24]([CH3:33])=[C:25]2[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[O:27][CH2:26]2)(=O)=O>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:33][C:24]1[C:23](/[CH:10]=[CH:11]/[CH3:12])=[CH:31][CH:30]=[C:29]2[C:25]=1[CH2:26][O:27][C:28]2=[O:32]

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 49761691Potassium trans-1-propenyltrifluoroborateHCID 866472924-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate

Produkt 1

HCID 86709439(E)-4-Methyl-5-(prop-1-en-1-yl)isobenzofuran-1(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To Pd(dppf)Cl2 (0.220 g, 0.338 mmol), K3PO4 (6.75 mL, 1 M in water, 6.75 mmol) in THF (22 mL) was added potassium (E)-trifluoro(prop-1-en-1-yl)borate (0.749 g, 5.06 mmol) and 4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate (I-4B, Method 2, step D, 1.0 g, 3.38 mmol). The reaction mixture was de-gassed for 10 min and the resulting mixture was stirred overnight at 70° C. The reaction mixture was cooled to room temperature and diluted with EtOAc and water. After separation of layers, the aqueous layer was extracted with EtOAc, and combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, concentrated and purified by silica gel column chromatography using (0-50%) acetone-hexanes as mobile phase to give the title compound. LC/MS: [(M+1)]+=189

Aufarbeitung

  1. customThe reaction mixture was de-gassed for 10 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additiondiluted with EtOAc and water
  4. customAfter separation of layers
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washwere washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6c459e9137864382bdb94b6ce372bf7e
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952166B2

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