Potassium Phosphate, Tribasic → 2-(2,4,6-Trimethylphenyl)-3-methoxy-cyclopent-2-enone
Reaktionsgleichung
Br[C:2]1[C:3](=[O:9])[CH2:4][CH2:5][C:6]=1[O:7][CH3:8].[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[CH3:8][O:7][C:6]1[CH2:5][CH2:4][C:3](=[O:9])[C:2]=1[C:12]1[C:13]([CH3:18])=[CH:14][C:15]([CH3:17])=[CH:16][C:11]=1[CH3:10]Komponenten
7
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
To a suspension of 2-bromo-3-methoxy-cyclopent-2-enone (32.3 g 169 mmol), 2,4,6-trimethylphenyl boronic acid (29.5 g, 180 mmol) and freshly ground potassium phosphate (63.7 g) in degassed toluene (800 ml) under N2 is added Pd(OAc)2 (896 mg, 8 mmol) and S-Phos (1.64 g, 4 mmol), and the reaction heated to 90° C. with stirring under N2 overnight. The reaction is partitioned between ethyl acetate (500 ml) and water (500 ml), and the organic layer is removed and the aqueous phase is extracted with ethyl acetate (2×300 ml). The combined organic extracts are evaporated under reduced pressure and the residue is purified to give 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (30.7 g).
Aufarbeitung
- customThe reaction is partitioned between ethyl acetate (500 ml) and water (500 ml)
- customthe organic layer is removed
- extractionthe aqueous phase is extracted with ethyl acetate (2×300 ml)
- customThe combined organic extracts are evaporated under reduced pressure
- customthe residue is purified
Quellen und Nachweise
- ORD-Eintrag
- ord-7dd1b5ee05ca43718b484008c801776e
- Quelldatensatz
- uspto-grants-2014_11
- Patentnummer
- US08889595B2
Notizen zur Reaktion
Wird geladen…