Hydrochloric Acid → (4E)-5-(2-pyridyl)-4-pentenoic acid

HRID 1741819Notes

Reaction equation

HRID 1741819 reaction equation
[H-].[Na+].[Cl-].[C:4]([CH2:7][CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:6])=[O:5].[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH:35]=O.Cl>CS(C)=O.O>[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1/[CH:35]=[CH:9]/[CH2:8][CH2:7][C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 142732-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 21180642(3-Carboxypropyl)(triphenyl)phosphanium chloride

Product 1

HCID 19010766(4E)-5-(2-pyridyl)-4-pentenoic acidYield 24.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of sodium hydride (3.04 g; 60% in mineral oil) in dimethyl sulfoxide (100 ml) was heated at 80° C. for 40 minutes. Then the solution was cooled. To the solution was added (3-carboxypropyl)triphenylphosphonium chloride (15.9 g) portionwise at ambient temperature. After 30 minutes, 2-pyridinecarbaldehyde (3.96 g) was added at ambient temperature and then the mixture was stirred for 2 hours. Water was added to the mixture and acidified to pH 5 with 1N hydrochloric acid. The mixture was extracted with ethyl acetate and combined organic layer was washed with brine, dried, and concentrated. The residue was chromatographed on silica gel ethyl acetate:methanol=10:1) to give (4E)-5-(2-pyridyl)-4-pentenoic acid (1.6 g).

Workup

  1. temperatureThen the solution was cooled
  2. extractionThe mixture was extracted with ethyl acetate and combined organic layer
  3. washwas washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel ethyl acetate

Sources & evidence

ORD record
ord-645699a344174d648f69bf897431ff3d
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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