2-Furanacrylic acid → 3-(Oxolan-2-yl)propanoic acid

HRID 76267

Reaction equation

HRID 76267 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8]([OH:10])=[O:9]>CO.[Pd]>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 6434022-Furanacrylic acid

Product 1

HCID 2631613-(Oxolan-2-yl)propanoic acidYield 93.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

(E)-3-(Furan-2-yl)acrylic acid (10 g, 72.4 mmol) was treated with Pd/C (1 g) in MeOH (100 mL). The mixture was heated at 60° C. at 60 psi under H2 for 12 hrs. After filtering off the catalyst, the filtrate was concentrated to afford 9.8 g (93%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.42-1.56 (m, 1 H) 1.77-1.96 (m, 4 H) 1.93-2.07 (m, 1 H) 2.41-2.56 (m, 2 H) 3.71-3.79 (m, 1 H) 3.82-3.94 (m, 2 H); MS (DCI/NH4+) m/z 145 (M+H)+.

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-750eb201c19d40f4957d2fadcbc9634f
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Linked notes

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