Methyl 4-[3-(3-benzyloxy-2-pyridyl)prop-2-enyl]benzoate → Methyl 4-[3-(3-hydroxy-2-pyridyl)propyl]benzoate

HRID 2395077Notes

Reaction equation

HRID 2395077 reaction equation
C([O:8][C:9]1[C:10]([CH:15]=[CH:16][CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>C(O)C.CCOC(C)=O.[Pd]>[OH:8][C:9]1[C:10]([CH2:15][CH2:16][CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 54508749Methyl 4-[3-(3-benzyloxy-2-pyridyl)prop-2-enyl]benzoate

Product 1

HCID 18974066Methyl 4-[3-(3-hydroxy-2-pyridyl)propyl]benzoateYield 77.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-[3-(3-benzyloxy-2-pyridyl)prop-2-enyl]benzoate (1.5 g, 4.2 mmol) was dissolved in ethanol (5 ml) and EtOAc (15 ml), treated with 10% palladium on carbon (0.15 g) and placed under a hydrogen atmosphere. The mixture was stirred at ambient temperature for 10 hours and filtered and evaporated to give methyl 4-[3-(3-hydroxy-2-pyridyl)propyl]benzoate as a yellow oil (0.88 g, 77%).

Workup

  1. filtrationfiltered
  2. customevaporated

Sources & evidence

ORD record
ord-5f873da4a15f4cd8b3bf0753b4f869d3
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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