HCID 22007098, compound → HCID 70165563, compound

HRID 323766Notes

Reaction equation

HRID 323766 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]#[C:11][CH2:12][OH:13])[C:4]=2[CH2:3][CH2:2]1>N1C=CC=CC=1.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9](/[CH:10]=[CH:11]\[CH2:12][OH:13])[C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 22007098HCID 22007098, compound

Product 1

HCID 70165563HCID 70165563, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 3-(2,3-dihydrobenzofuran-4-yl)prop-2-yn-1-ol (6.2 mmol) and Pd/C (300 mg) in 20 mL of pyridine was shaken under an atmosphere of H2 (10 psi) until no starting material remained (8 h). The crude reaction mixture was filtered to remove the catalyst and the catalyst was washed with ether. The filtrate was concentrated in vacuo to provide 1.1 g of the desired product as a yellow oil (quantitative yield).

Workup

  1. custom(8 h)
  2. customThe crude reaction mixture
  3. filtrationwas filtered
  4. customto remove the catalyst
  5. washthe catalyst was washed with ether
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-319820a5df084a66a77be1a2203c901e
Source dataset
uspto-grants-2001_04
Patent number
US06214869B1

Reaction notes

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