Cesium carbonate → HCID 59407851, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH3:10])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:17]([O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[C:18]#[CH:19].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[Cl-].[Na+].O.CC#N.CC#N.Cl[Pd]Cl.C(#N)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:19]#[C:18][CH2:17][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)=[CH:3][C:4]=1[CH3:10]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 4-bromo-2-methylanisole (3.02 g), cesium carbonate (12.7 g), 2-(2-propynyloxy)tetrahydropyran (3.16 ml), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (429 mg), bis(acetonitrile)palladium(II) dichloride (77.8 mg) and acetonitrile (100 ml) was stirred at 80° C. for 5 hr. The reaction mixture was added to brine, 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=100:0-90:10) to give the object product (1.76 g) as a pale-brown 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=100:0-90:10)
Sources & evidence
- ORD record
- ord-2444411ee20843a59a360217eaba9d13
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129361B2
Reaction notes
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