Reaction equation
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][CH2:57][CH2:56][C:55]2([CH3:61])[CH3:60]>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][CH2:57][CH2:56][C:55]3([CH3:60])[CH3:61])[CH2:43][CH2:42]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A vial was charged with Pd(OAc)2 (2.40 mg, 10.7 μmol), XPhos (10.2 mg, 0.02 mmol), potassium carbonate (148 mg, 1.07 mmol), potassium cyclopropyltrifluoroborate (58.0 mg, 0.39 mmol) and 8-chloro-4,4-dimethyl-3,4-dihydro-2H-chromene-6-carbaldehyde (80.0 mg, 0.36 mmol). The mixture was dissolved in cyclopropylmethyl ether (2.00 mL) and water (0.20 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 0-15% EtOAc/hexanes to afford the desired product as a yellow oil.
Workup
- customwater (0.20 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 0-15% EtOAc/hexanes
Sources & evidence
- ORD record
- ord-d8701f8edb934c41b3d0a055f6779757
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08742110B2
Linked notes
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