Tetrahydrofuran → Picolinic acid

HRID 1774011Notes

Reaction equation

HRID 1774011 reaction equation
C(OC(=O)/C=[C:11](/[C:13]1C=CC=C[N:14]=1)\C)C1C=CC=CC=1.C([O:27]C(=O)/C=C(\C1C=CC=CN=1)/C)C1C=CC=CC=1.[CH2:39]1[CH2:43][O:42][CH2:41][CH2:40]1>[Pd]>[N:14]1[CH:13]=[CH:11][CH:43]=[CH:39][C:40]=1[C:41]([OH:27])=[O:42]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 89648652HCID 89648652, compoundHCID 89648653HCID 89648653, compound

Product 1

HCID 1018Picolinic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
50 °C

Procedure

To a solution under N2 of (E)-3-pyridin-2-yl-but-2-enoic acid benzyl ester (1.40 g, 5.53 mmol, 1.00 eq.) and (Z)-3-pyridin-2-yl-but-2-enoic acid benzyl ester (320 mg, 1.26 mmol, 0.23 eq.) in THF (50 mL), palladium on activated carbon (10 wt. %, 200 mg) was added. The flask was evacuated and refilled with H2 (3×). The black suspension was stirred at 50° C. under an H2-atmosphere for 16 hours. The black suspension was filtered through Celite. The Celite was rinsed with THF and the filtrate was concentrated in vacuo. The residue was dissolved in water (3 mL), MeCN (1 mL) and formic acid (0.5 mL). The solution was directly purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions, extremely polar method) and concentrated in vacuo to give the desired acid as a white solid.

Workup

  1. customThe flask was evacuated
  2. additionrefilled with H2 (3×)
  3. filtrationThe black suspension was filtered through Celite
  4. washThe Celite was rinsed with THF
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe residue was dissolved in water (3 mL)
  7. customThe solution was directly purified by prep
  8. concentrationHPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions, extremely polar method) and concentrated in vacuo

Sources & evidence

ORD record
ord-14730138ed8446f392a4bd8c31523a0e
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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