Reaction #792145

ord-f370b04507bd477a8239c8b264bf7080

Reaction equation

CC(C)COc1ccc(C(=O)/C=C/c2ccccn2)c(O)c1
(E)-1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one
CC(C)COc1ccc(C(=O)CCc2ccccn2)c(O)c1
final compound
Yield 84.7%
CC(C)COc1ccc(C(=O)CCc2ccccn2)c(O)c1
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one
Yield 84.7%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

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

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09173424B2uspto-grants-2015_11