Tetrahydrofuran → Methyl 2-(3-phenoxyphenoxy)pyrid-3-ylacetate

HRID 467044Notes

Reaction equation

HRID 467044 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[O:11][C:12]1[C:17]([CH:18]=O)=[CH:16][CH:15]=[CH:14][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(CSC)=[O:25].C1[CH2:33][O:32][CH2:31]C1>CO.O.Cl>[O:1]([C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[O:11][C:12]1[C:17]([CH2:18][C:31]([O:32][CH3:33])=[O:25])=[CH:16][CH:15]=[CH:14][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 197718832-(3-Phenoxyphenoxy)-3-formylpyridine

Product 1

HCID 54201529Methyl 2-(3-phenoxyphenoxy)pyrid-3-ylacetate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of the aldehyde (3.03 g, 0.01 mol) and methyl methylsulphinylmethyl sulphide (1.29 g, 0.01 mol) in dry THF (8 ml) at room temperature was added dropwise a solution of Triton B (2.5 ml, 40% in methanol). The resultant solution was heated to reflux for 1 hour, cooled and then diluted with water. Extraction with dichloromethane followed by drying and evaporation yielded a yellow oil which was dissolved in methanolic hydrogen chloride (100 ml) and allowed to stand overnight. The methanol was evaporated and the residue treated with saturated sodium bicarbonate solution and then extracted with dichloromethane. The combined organic extracts were dried, filtered and evaporated. The residue was chromatographed on silica gel (eluent hexane-ether, 1:1) to afford methyl 2-(3-phenoxyphenoxy)pyrid-3-ylacetate (1.35 g) as a pale yellow oil;

Workup

  1. temperatureto reflux for 1 hour
  2. temperaturecooled
  3. extractionExtraction with dichloromethane
  4. customby drying
  5. customevaporation
  6. customyielded a yellow oil which
  7. customThe methanol was evaporated
  8. additionthe residue treated with saturated sodium bicarbonate solution
  9. extractionextracted with dichloromethane
  10. customThe combined organic extracts were dried
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue was chromatographed on silica gel (eluent hexane-ether, 1:1)

Sources & evidence

ORD record
ord-79d80232e40244b9a5976818c5686400
Source dataset
uspto-grants-1992_10
Patent number
US05158954

Reaction notes

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