Trifluoroacetic acid → 3-(2,4-Dihydroxy-phenyl)-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

HRID 2275243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2275243
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:15])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.C[C:17]([CH3:20])([O-:19])[CH3:18].[Na+].F[B-](F)(F)F.[C:27]([PH+](C(C)(C)C)C(C)(C)C)([CH3:30])(C)[CH3:28].FC(F)(F)C(O)=[O:43].P([O-])([O-])(O)=O.[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(Cl)Cl.CO.C1(C)C=CC=CC=1>[OH:43][C:28]1[CH:20]=[C:17]([OH:19])[CH:18]=[CH:30][C:27]=1[CH:8]1[CH2:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]([CH3:13])([CH3:14])[C:9]1=[O:15]

Komponenten

10

Edukt 5

HCID 6422Trifluoroacetic acidHCID 24450Potassium Phosphate, DibasicHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 130110077-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one2×HCID 23676156Sodium t-butoxide

Produkt 1

HCID 668346193-(2,4-Dihydroxy-phenyl)-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-oneAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 10 g), 2-bromo-1,3-dihydroxytetrahydropyranbenzene (Compound Z9, 20.98 g), sodium t-butoxide (5.88 g), palladium acetate (550 mg) and tri-t-butylphosphonium tetrafluoroborate (710 mg), toluene (40 mL) was added and the mixture was stirred and heated at 70° C. under nitrogen atmosphere for 6 hr. After cooling, the reaction mixture was added with methanol (38 mL) and trifluoroacetic acid (14.54 mL) at room temperature, and then stirred at room temperature overnight. To the resulting residues, methylene chloride and saturated dipotassium hydrogen phosphate were added and the organic layer was washed with saturated brine. Thereafter, the organic layer was dried over magnesium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (5.53 g, 36%).

Aufarbeitung

  1. temperatureAfter cooling
  2. stirringstirred at room temperature overnight
  3. washthe organic layer was washed with saturated brine
  4. dry with materialThereafter, the organic layer was dried over magnesium sulfate
  5. customThe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-518f3eeb8dac4b1c99c3c06bab242eae
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126931B2

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