Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethenyl]benzoate → Methyl 4-[2-(3-hydroxy-2-pyridyl)ethyl]benzoate

HRID 2395069Notes

Reaction equation

HRID 2395069 reaction equation
C([O:8][C:9]1[C:10]([CH:15]=[CH:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CCOC(C)=O.CCO>[OH:8][C:9]1[C:10]([CH2:15][CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 54224333Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethenyl]benzoate

Product 1

HCID 18973722Methyl 4-[2-(3-hydroxy-2-pyridyl)ethyl]benzoateYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethenyl]benzoate (2.0 g, 5.8 nnol) was partially dissolved in EtOAc (20 ml) and EtOH (10 ml). The reaction vessel was flushed with argon, palladium-on-carbon (0.2 g, 10%) was added and the reaction was flushed with argon followed by hydrogen. The reaction was stirred at ambient temperature for 18 hours, filtered and evaporated to give methyl 4-[2-(3-hydroxy-2-pyridyl)ethyl]benzoate as a pale orange solid (1.3 g, 90%) which was used without further purification.

Workup

  1. customThe reaction vessel was flushed with argon, palladium-on-carbon (0.2 g, 10%)
  2. additionwas added
  3. customthe reaction was flushed with argon
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c13f2d348d3245c18558dba0db1118b4
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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