Tetrahydrofuran → Phenyl-(pyridin-3-yloxy)acetic acid methyl ester

HRID 352198Notes

Reaction equation

HRID 352198 reaction equation
[Na].[OH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.Br[CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([OH:13])=[O:12].O1CCC[CH2:21]1>>[CH3:21][O:13][C:11](=[O:12])[CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[O:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 97919Bromo(phenyl)acetic acidHCID 667964713-Hydroxypyridine sodium salt

Product 1

HCID 69849520Phenyl-(pyridin-3-yloxy)acetic acid methyl ester

Procedure

To a slurry of 3-hydroxypyridine sodium salt, 4.6 g (26.4 mmol) in 200 mL of tetrahydrofuran was added 5.0 g (22.0 mmol) of alpha-bromophenylacetic acid. The reaction mixture was refluxed for two hours, cooled to rt. and concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and water. The mixture was washed with saturated NaHCO3, washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by column chromatography using MeOH/chloroform as eluent and concentrated to dryness to give 2.8 g of the desired mixture of isomers as a dark oil. MS (ion spray) 244.1 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed for two hours
  2. concentrationand concentrated to dryness
  3. customThe residue was partitioned between 20% isopropanol/chloroform and water
  4. washThe mixture was washed with saturated NaHCO3
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by column chromatography
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-42abf798e6444acfb0d26abb7374e7c0
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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