3-Thiophen-2-ylprop-2-enoic acid → 3-(2-Thienyl)propanoic acid

HRID 1768911Notes

Reaction equation

HRID 1768911 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([OH:10])=[O:9]>[Pd].O1CCCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 928683-Thiophen-2-ylprop-2-enoic acid

Product 1

HCID 7031693-(2-Thienyl)propanoic acidYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on carbon (10%, 4.2 g) was added in one portion to a solution of 3-(2-thienyl)acrylic acid (15.59 g, 0.10 mol) in tetrahydrofuran (130 mL). The mixture was subjected to Parr hydrogenation conditions (45 psi, room temperature) for about 24 hours. Following filtration through Celite, the filtrate was concentrated down to dryness and gave a brown-colored solid which was recrystallized from water. There was isolated 9.32 g (60%) of the title compound as a mixture of white and tan colored needles, m.p. 58°-60° C. (m.p. lit. 62°-62.5° C.); 1H NMR (CD3SOCD3) 6 12.2 (br s, 1H), 7.23-7.21 (m, 1H), 6.89-6.86 (m, 1H), 6.82-6.81 (m, 1H), 2.99 (t, J=7.4 Hz, 2H), 2.53 (t, J=7.4 Hz, 2H); 13C NMR (CD3SOCD3) ppm 173.42, 143.39, 126.90, 124.70, 123.72, 35.61, 24.70; IR (KBr, cm-1) 3102-3036, 2922, 2644, 1706, 1440, 1408, 1310, 1232, 1220, 938, 848, 828, 714, 692; MS m/z (MH+) 157.

Workup

  1. filtrationfiltration through Celite
  2. concentrationthe filtrate was concentrated down to dryness
  3. customgave a brown-colored solid which
  4. customwas recrystallized from water

Sources & evidence

ORD record
ord-3b383234ec114184aac94fac6d7d0100
Source dataset
uspto-grants-1995_01
Patent number
US05380713

Reaction notes

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