Sodium → HCID 20260938, compound

HRID 1583377Notes

Reaction equation

HRID 1583377 reaction equation
[Na].C([O:4][C:5](=[O:24])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:10][C:9]=1[C:21](=O)[CH3:22])C>C(O)C>[CH3:22][C:21]1[C:9]2[CH:10]=[C:11]([CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:5]([OH:4])=[O:24]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 54366831HCID 54366831, compound

Product 1

HCID 20260938HCID 20260938, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (0.50 g.) was dissolved in ethanol (10 ml.) and a solution of 2-acetyl-4-(3-pyridylmethyl)phenoxyacetic acid ethyl ester (4.70 g.) in ethanol (15 ml.) was added. The mixture was heated under reflux for 3 hours and then evaporated. The residue was dissolved in water and the solution was washed several times with ether. The aqueous layer was acidified with glacial acetic acid to give a gummy solid which was filtered off, washed with water, dried and chromatographed on silica gel. Elution with chloroform gave some impurity and then further elution with chloroform/methanl (9:1) gave a solid which was crystallized from ethanol to give 3-methyl-5-(3-pyridylmethyl)benzofuran-2-carboxylic acid (0.75 g.) m.p. 223-225° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customevaporated
  4. dissolutionThe residue was dissolved in water
  5. washthe solution was washed several times with ether
  6. customto give a gummy solid which
  7. filtrationwas filtered off
  8. washwashed with water
  9. customdried
  10. customchromatographed on silica gel
  11. washElution with chloroform
  12. customgave some impurity
  13. washfurther elution with chloroform/methanl (9:1)
  14. customgave a solid which
  15. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-039eb0f9770242d499a6aa5227f709d5
Source dataset
uspto-grants-1985_11
Patent number
US04551468

Reaction notes

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