Ethyl 3-(5-hydroxypyridin-2-yl)prop-2-enoate → HCID 20213294, compound

HRID 602463Notes

Reaction equation

HRID 602463 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=1>[Pd].C(O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 67270386Ethyl 3-(5-hydroxypyridin-2-yl)prop-2-enoate

Product 1

HCID 20213294HCID 20213294, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The mixture of ethyl 3-(5-hydroxypyridin-2-yl)acrylate (2.30 g, 11.9 mmol, step 1 of Example 5) and 10 wt. % palladium on carbon (230 mg) in ethanol (5 mL) was stirred under hydrogen (1 atom) at room temperature for 24 h. The mixture was filtered through a pad of Celite, and washed with ethanol and the filtrate was concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (1:1) to give 1.51 g (65%) of the title compound as a yellow crystal.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashed with ethanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-608624b380d94fb4b29433c45bcba838
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

Loading…