Potassium Carbonate → Benzopyran

HRID 1282413Notes

Reaction equation

HRID 1282413 reaction equation
C[Si]([C:5]#[CH:6])(C)C.[C:7](=[O:10])([O-])[O-].[K+].[K+].F[C:14](F)(F)[C:15]([C:17](F)(F)F)=O.[CH2:23]([Li])[CH2:24][CH2:25]C.[H-].[Na+]>CO.S([O-])([O-])(=O)=O.[Ba+2].[Pd+2].S([O-])([O-])(=O)=O.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:10]1[C:7]2[CH:23]=[CH:24][CH:25]=[CH:5][C:6]=2[CH:17]=[CH:15][CH2:14]1

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 12695HexafluoroacetoneHCID 24758Sodium hydrideHCID 66111Trimethylsilylacetylene2×HCID 178418339Butyllithium

Product 1

HCID 9211Benzopyran

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 17887766Palladium barium sulphateCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

According to Tetrahedron Letters, 1993, 34, 1815-1818, a compound (IIf) and trimethylsilyl acetylene are subjected to cross-coupling reaction in the presence of copper(I) iodide and tetrakis(triphenylphosphine)palladium and the resulting trimethylsilyl acetylene compound is treated with potassium carbonate in methanol to give a compound represented by the formula (XIX) set forth below. This compound is reacted with hexafluoroacetone using n-butyllithium to give a compound represented by the formula (XX). This compound is reduced with a palladium-barium sulfate catalyst under a hydrogen atmosphere to give a compound represented by the formula (XXI). This compound is reacted with sodium hydride to give a benzopyran derivative represented by the formula (XXII).

Workup

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Sources & evidence

ORD record
ord-ea37e5f848e64a47b6e407f1756ff9df
Source dataset
uspto-grants-2002_09
Patent number
US06455708B1

Reaction notes

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