(6-Benzyloxy-pyridin-3-yloxy)-acetic acid ethyl ester → (6-Hydroxy-pyridin-3-yloxy)-acetic acid ethyl ester

HRID 417093Notes

Reaction equation

HRID 417093 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[CH:8]=[N:9][C:10]([O:13]CC2C=CC=CC=2)=[CH:11][CH:12]=1)[CH3:2]>[Pd]>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[CH:8]=[N:9][C:10]([OH:13])=[CH:11][CH:12]=1)[CH3:2]

Participants

3

Reactant 1

HCID 66619330(6-Benzyloxy-pyridin-3-yloxy)-acetic acid ethyl ester

Product 1

HCID 178473014(6-Hydroxy-pyridin-3-yloxy)-acetic acid ethyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The suspension of 0.64 g (2.23 mmol) (6-benzyloxy-pyridin-3-yloxy)-acetic acid ethyl ester and 0.064 g 10% palladium on charcoal was hydrogenated for 1 h at 1.7 bar. The reaction mixture was filtered over Dicalite Speed Plus, washed with ethanol and the filtrate was treated with silica gel and evaporated. The residue was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) with a gradient from heptane:ethyl acetate (100:0 to 0:100) followed by ethyl acetate:methanol (100:0 to 50:50) to give the product as a colorless solid (91%). MS (Turbo Spray): m/z=198.0 [M+H].

Workup

  1. filtrationThe reaction mixture was filtered over Dicalite Speed Plus
  2. washwashed with ethanol
  3. additionthe filtrate was treated with silica gel
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5eee0917329147eb875c388903569cef
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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