Pyridine → HCID 22503243, compound

HRID 1006931Notes

Reaction equation

HRID 1006931 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1.C[Si]([C:19]#[CH:20])(C)C.N1C=CC=CC=1>C(N(CC)CC)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:19]#[CH:20])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 66111TrimethylsilylacetyleneHCID 22502881HCID 22502881, compound

Product 1

HCID 22503243HCID 22503243, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1-[(1,3-Dioxolan-2-yl)methyloxy]-4-iodobenzene (36.3 g) and trimethylsilylacetylene (50.0 g) were reacted in the presence of bistriphenylphosphinepalladium dichloride (2.50 g) and cuprous iodide (1.25 g), in triethylamine (140 ml) and pyridine (70 ml) at 60° C. for 2 hr. The reaction solution was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried and concentrated. The resulting residue was dissolved in methanol and treated with 2N sodium hydroxide, to give 20.1 g of the title compound.

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe resulting organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe resulting residue was dissolved in methanol
  6. additiontreated with 2N sodium hydroxide

Sources & evidence

ORD record
ord-66ea8f90d5444de7b7d0fc92da7fc457
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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