HCID 22503258, compound → HCID 67271323, compound

HRID 597898Notes

Reaction equation

HRID 597898 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][CH:10]([OH:12])[CH3:11])=[N:6][CH:7]=1.[H][H]>CCOC(C)=O.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][CH:10]([OH:12])[CH3:11])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 22503258HCID 22503258, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67271323HCID 67271323, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The 4-(5-bromo-pyridin-2-yl)-but-3-yn-2-ol prepared in Step 1 (2.26 g, 0.010 mol) was dissolved in EtOAc (50 mL). Lindlar's catalyst (1.13 g) was added and the mixture was shaken on a Parr shaker under 55 psi hydrogen for 16 h. The mixture was filtered and concentrated. The residue was chromatographed (SiO2, 9/1 to 4/1 hexane/EtOAc) to afford 4-(5-bromo-pyridin-2-yl)-but-3-en-2-ol as a clear oil (1.12 g, 49%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was chromatographed (SiO2, 9/1 to 4/1 hexane/EtOAc)

Sources & evidence

ORD record
ord-3d38aa97e027431fb010887885e13949
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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