3-Fluorobenzaldehyde → HCID 57435649, compound

HRID 1373005Notes

Reaction equation

HRID 1373005 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:3][CH:2]=1.[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O>C(OC(=O)C)(=O)C.C(N(CC)CC)C>[F:13][C:14]1[CH:15]=[C:16](/[CH:17]=[C:7](\[C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 680093-FluorobenzaldehydeHCID 736321Ethyl pyridine-4-acetate

Product 1

HCID 57435649HCID 57435649, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of ethyl 4-pyridylacetate (25.0 g, 0.151 mol) and 3-fluorobenzaldehyde (20.7 g, 0.167 mol) in a mixture of acetic anhydride (100 mL) and triethylamine (20 mL) was heated under reflux for 5.5 hours. After standing to cool, the reaction mixture was concentrated. The residue was diluted with ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium hydrogencarbonate solution twice and brine, dried over anhydrous sodium sulfate and then concentrated. The residue was subjected to silica gel column chromatography (eluent; hexane, hexane:ethyl acetate=9:1), to give the title compound (25.5 g, 62%) as a red-orange oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5.5 hours
  3. temperatureto cool
  4. concentrationthe reaction mixture was concentrated
  5. additionThe residue was diluted with ethyl acetate
  6. extractiona saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layers were washed with a saturated aqueous sodium hydrogencarbonate solution twice
  8. dry with materialbrine, dried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3ea8ef0b2a3e4c948e0caf1049b2a27c
Source dataset
uspto-grants-2007_01
Patent number
US07160892B2

Reaction notes

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