HCID 66852260, compound → 1-[2-Hydroxy-4-(2-methylpropoxy)phenyl]-3-(2-pyridinyl)-1-propanone

HRID 704963Notes

Reaction equation

HRID 704963 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[CH:4][C:3]=1[C:13](=[O:22])/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1>CCOC(C)=O.[Pd]>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH:5]=[CH:4][C:3]=1[C:13](=[O:22])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

4

Reactant 1

HCID 66852260HCID 66852260, compound

Product 1

HCID 498695501-[2-Hydroxy-4-(2-methylpropoxy)phenyl]-3-(2-pyridinyl)-1-propanoneYield 84.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a 200 mL round-bottomed flask, (E)-1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one (1.08 g, 3.63 mmol) and 80 mg of 10% Pd/C was mixed together in wet EtOAc (50 ml). Hydrogenation was conducted at atmospheric pressure room temperature until the starting material was gone. The catalyst was filtered and the crude was purified by chromatography on silica gel (25% EtOAc/hexane) to provide 0.92 g of final compound (82%) as off white solid.

Workup

  1. customwas conducted at atmospheric pressure room temperature until the starting material
  2. filtrationThe catalyst was filtered
  3. customthe crude was purified by chromatography on silica gel (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-f370b04507bd477a8239c8b264bf7080
Source dataset
uspto-grants-2015_11
Patent number
US09173424B2

Reaction notes

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