Methanol → HCID 13687916, compound

HRID 569798Notes

Reaction equation

HRID 569798 reaction equation
Cl[CH:2]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([O:21][CH3:22])=[O:20])[CH:13]=[CH:12]2)[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH3:25][OH:26]>>[CH3:25][O:26][CH:2]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([O:21][CH3:22])=[O:20])[CH:13]=[CH:12]2)[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 13687914HCID 13687914, compound

Product 1

HCID 13687916HCID 13687916, compoundYield 94%

Procedure

52 mg (0.17 mmol) of methyl 6-[1-chloro-1-(3-pyridyl) methyl]-2-naphthoate and 8 mg (0.18 mmol) of sodium hydride dispersion (55%) in 4 ml of absolute methanol are heated under reflux for 6 hours. After the reaction mixture has been evaporated, the residue is taken up in sodium bicarbonate solution, which is extracted with ethyl acetate. After the ethyl acetate phase has been dried and evaporated in vacuo, the residue is chromatographed on silica gel using ethyl acetate. 48.2 mg (94%) of methyl 6-[1-methoxy-1-(3-pyridyl)methyl]-2-naphthoate are obtained. RF (ethyl acetate/cyclohexane 1:1): 0.17.

Workup

  1. temperatureunder reflux for 6 hours
  2. customAfter the reaction mixture has been evaporated
  3. extractionwhich is extracted with ethyl acetate
  4. dry with materialAfter the ethyl acetate phase has been dried
  5. customevaporated in vacuo
  6. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-0e927b1359dd47119a49a3d351edc530
Source dataset
uspto-grants-1988_03
Patent number
US04734406

Reaction notes

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