Cesium carbonate → HCID 59407658, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:16]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)[C:17]#[CH:18].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>CC#N.CC#N.Cl[Pd]Cl.O.C(#N)C>[CH2:8]([C:4]1[CH:3]=[C:2]([C:18]#[C:17][CH2:16][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH:7]=[CH:6][CH:5]=1)[CH3:9]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 1-bromo-3-ethylbenzene (9.79 g), cesium carbonate (45.0 g), 2-(2-propynyloxy)tetrahydropyran (11.2 ml), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (1.51 g), bis(acetonitrile)palladium(II) dichloride (274 mg) and acetonitrile (300 ml) was stirred at 90° C. for 10 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-95:5) to give the object product (5.25 g) as a yellow oil.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washwashed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1-95:5)
Sources & evidence
- ORD record
- ord-663f7a92d3344da5a80ea67fe0ac8ab4
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129361B2
Reaction notes
Loading…