methyl (2Z,4E)-5-(benzofuran-2-yl)-2-methoxy-2,4-pentadienoate → (2Z,4E)-5-(Benzofuran-2-yl)-2-methoxy-2,4-pentadienoic acid

HRID 377363Notes

Reaction equation

HRID 377363 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1/[CH:10]=[CH:11]/[CH:12]=[C:13](\[O:18][CH3:19])/[C:14]([O:16]C)=[O:15].CCO.O>O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1/[CH:10]=[CH:11]/[CH:12]=[C:13](\[O:18][CH3:19])/[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 11076120methyl (2Z,4E)-5-(benzofuran-2-yl)-2-methoxy-2,4-pentadienoateHCID 19096565Water ethanol

Product 1

HCID 10955790(2Z,4E)-5-(Benzofuran-2-yl)-2-methoxy-2,4-pentadienoic acidYield 84.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of methyl (2Z,4E)-5-(benzofuran-2-yl)-2-methoxy-2,4-pentadienoate (1.0 g, 3.87 mmol) in EtOH/water 1/1 (80 ml) potassium hydroxide (0.43 g, 7.66 mmol) was added. The solution was refluxed for 1 hour, then it was cooled to RT and poured into water (200 ml). After acidification to pH 2 (1N HCl) the resulting suspension was extracted with EtOAc (3×50 ml). The organic phase was washed with water (2×30 ml), dried (MgSO4) and concentrated to give a yellow solid. This was repeatedly washed with CH2Cl2 and dried to give the pure title compound (0.80 g, 3.28 mmoles, yield 84.6%) as yellow crystals, m.p.=206°.

Workup

  1. temperatureThe solution was refluxed for 1 hour
  2. extractionAfter acidification to pH 2 (1N HCl) the resulting suspension was extracted with EtOAc (3×50 ml)
  3. washThe organic phase was washed with water (2×30 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a yellow solid
  7. washThis was repeatedly washed with CH2Cl2
  8. customdried

Sources & evidence

ORD record
ord-b370ab37ba6942fcab67247a4778189d
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Reaction notes

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