HCID 57815270, compound → HCID 57815493, compound

HRID 1510721Notes

Reaction equation

HRID 1510721 reaction equation
FC(F)(F)S(O[C:7]1[C:12](=[O:13])[CH:11]=[C:10]([CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[O:9][CH:8]=1)(=O)=O>C(#N)C.C(O)C#C.C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[OH:9][CH2:8][C:7]#[C:12][C:7]1[C:12](=[O:13])[CH:11]=[C:10]([CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[O:9][CH:8]=1

Participants

7

Reactant 1

HCID 57815270HCID 57815270, compound

Product 1

HCID 57815493HCID 57815493, compoundYield 105.1%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 7859Propargyl alcoholSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 16 g of 4-oxo-6-((tetrahydro-2H-pyran-2-yloxy)methyl)-4H-pyran-3-yl trifluoromethanesulfonate in 100 mL of acetonitrile, 5.1 mL of propargyl alcohol, 18 mL of triethylamine, 0.62 g of dichlorobis(triphenylphosphine)palladium(II) and 0.42 g of copper (I) iodide were added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 2 hours. The insoluble substance was filtered off, and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with chloroform:methanol=100:0 to 97:3 to obtain 6.2 g of 5-(3-hydroxy-1-propyn-1-yl)-2-((tetrahydro-2H-pyran-2-yloxy)methyl)-4H-pyran-4-one as a brown oily substance.

Workup

  1. filtrationThe insoluble substance was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe resultant residue was purified by flash silica gel column chromatography
  4. washelution with chloroform

Sources & evidence

ORD record
ord-ee2894d15e574196a9748dfd5f0ac9bd
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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