Triphenylphosphine → Methyl 2-benzoyl-6-ethyl-3,5-dihydroxy-phenylacetate

HRID 495183Notizen

Reaktionsgleichung

C([O:4][C:5]1[C:6]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:7]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:8]([CH2:15][CH3:16])=[C:9]([O:11]CC=C)[CH:10]=1)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:22]([C:6]1[C:5]([OH:4])=[CH:10][C:9]([OH:11])=[C:8]([CH2:15][CH3:16])[C:7]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19])(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Methyl 3,5-diallyloxy-2-benzoyl-6-ethylphenylacetate (0.29 g, 0.72 mmol) obtained in Example 5, Step 4 was dissolved in acetic acid (5.0 mL) in an atmosphere of argon. To the solution were added triphenylphosphine (74 mg, 0.28 mmol) and palladium (II) acetate (16 mg, 0.071 mmol), followed by stirring at 80° C. for 5 hours. To the reaction mixture were further added triphenylphosphine (0.15 g, 0.57 mmol) and palladium (II) acetate (32 mg, 0.14 mmol), followed by stirring at 100° C. for 13 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-3/1) to obtain Compound 5 (0.23 g, 60%).

Aufarbeitung

stirringby stirring at 100° C. for 13 hours
temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-3/1)

Quellen und Nachweise

ORD-Eintrag: ord-3d35b8883e314912a6f294d42a3a62b8
Quelldatensatz: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07538224B2

Notizen zur Reaktion

Wird geladen…