Hydrochloric Acid → HCID 67107791, compound

HRID 2177836Notes

Reaction equation

HRID 2177836 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]([O:14][CH3:15])=[O:13])=[C:9]([CH3:16])[CH:8]=[CH:7]2.[CH3:17][O-:18].[Na+].N1C=CC=CC=1.Cl>CO.O.[Cu](I)I>[CH3:17][O:18][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]([O:14][CH3:15])=[O:13])=[C:9]([CH3:16])[CH:8]=[CH:7]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10942334Sodium MethoxideHCID 67107751HCID 67107751, compound2×

Product 1

HCID 67107791HCID 67107791, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 8-bromo-2-methylnaphthalene-1-carboxylate (Intermediate 191, 1.0 g), sodium methoxide (25% wt/solution in methanol, 5 g), copper iodide (0.37 g), and pyridine (13 ml) in methanol (13 ml) was stirred and heated at reflux for 3 days. After cooling, the mixture was diluted with water, acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was separated, washed with 1M HCl and brine, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25% to give methyl 8-methoxy-2-methylnaphthalene-1-carboxylate (0.33 g) as a lilac oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 days
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with 1M HCl and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25%

Sources & evidence

ORD record
ord-26029e2eb27144f6bb94fb91f5c8cd3b
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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