Reaktionsgleichung
CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[K+].[K+].[CH:41]1([B-](F)(F)F)[CH2:43][CH2:42]1.[K+].Cl[C:50]1[CH:51]=[C:52]([CH:62]=[O:63])[CH:53]=[C:54]2[C:59]=1[O:58][C:57]([CH3:61])([CH3:60])[CH2:56][CH2:55]2>C1(OC)CC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:41]1([C:50]2[CH:51]=[C:52]([CH:62]=[O:63])[CH:53]=[C:54]3[C:59]=2[O:58][C:57]([CH3:60])([CH3:61])[CH2:56][CH2:55]3)[CH2:43][CH2:42]1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A vial was charged with Pd(OAc)2 (7.99 mg, 0.04 mmol), XPhos (25.5 mg, 0.05 mmol), potassium carbonate (148 mg, 1.07 mmol), potassium cyclopropyltrifluoroborate (58.0 mg, 0.39 mmol) and 8-chloro-2,2-dimethyl-3,4-dihydro-2H-chromene-6-carbaldehyde (80 mg, 0.36 mmol). The mixture was dissolved in cyclopropylmethyl ether (1.62 mL) and water (0.16 mL) and purged with Ar. The reaction mixture was then stirred at 100° C. overnight, cooled to room temperature and filtered through a pad of celite. The filtrate was concentrated under vacuum, and the crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes to afford the desired product as a pale-yellow oil.
Aufarbeitung
- customwater (0.16 mL) and purged with Ar
- temperaturecooled to room temperature
- filtrationfiltered through a pad of celite
- concentrationThe filtrate was concentrated under vacuum
- customthe crude residue was purified by silica gel chromatography
- washeluting with 0-20% EtOAc/hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-1d789b5d164446f4ab2bade875d161c1
- Quelldatensatz
- uspto-grants-2014_06
- Patentnummer
- US08742110B2
Verknüpfte Notizen
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