Reaction #792146

ord-9224b33b097a4dfc9e90a7776e8d074b

Reaction equation

O=C(/C=C/c1ccccn1)c1ccc2c(c1O)OCO2
(E)-1-(4-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(pyridin-2-yl)prop-2-en-1-one
O=C(CCc1ccccn1)c1ccc2c(c1O)OCO2
title compound
Yield 59.6%
O=C(CCc1ccccn1)c1ccc2c(c1O)OCO2
1-(4-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(pyridin-2-yl)propan-1-one
Yield 59.6%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto give a yellow solution
  2. 2
    FiltrationThe reaction mixture was filtered
  3. 3
    Otherevaporated
  4. 4
    Washthe solid residue was washed with diethylether
  5. 5
    Otherdried

Procedure

(E)-1-(4-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(pyridin-2-yl)prop-2-en-1-one (0.5 g, 1.857 mmol) was added to methanol (50 ml) to give a yellow solution. Palladium on carbon (0.05 g) was added. Product was hydrogenated while stirring till conversion was completed (checked by TLC). The reaction mixture was filtered, evaporated and the solid residue was washed with diethylether, and dried to yield 0.3 g (57%) of the title compound.

Source

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