Potassium Carbonate → Methyl 6-morpholinobenzofuran-2-carboxylate

HRID 1357190Notes

Reaction equation

HRID 1357190 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].C([O-])([O-])=O.[K+].[K+].[OH:13][C:14]1[CH:21]=[C:20]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:19]=[CH:18][C:15]=1[CH:16]=O>C(#N)C>[O:25]1[CH2:24][CH2:23][N:22]([C:20]2[CH:19]=[CH:18][C:15]3[CH:16]=[C:2]([C:3]([O:5][CH3:6])=[O:4])[O:13][C:14]=3[CH:21]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 98156592-Hydroxy-4-morpholin-4-yl-benzaldehyde

Product 1

HCID 15462828Methyl 6-morpholinobenzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl bromoacetate (3.0 g) and K2CO3 (3.0 g) were added to a solution of 2-hydroxy-4-morpholinobenzaldehyde (3.5 g) in acetonitrile (100 ml), and after heated reflux for 16 hours, the reaction solution was filtered and the mother liquor was concentrated under reduced pressure. MeOH (100 ml) and concentrated hydrochloric acid (10 ml) were added to the residue, and after reflux for 5 hours, the reaction solution was concentrated under reduced pressure. A saturated NaHCO3 aqueous solution (100 ml) was added to the residue prior to extraction with AcOEt, and the organic layer was dried with MgSO4 and then filtered and concentrated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=5/1) to obtain methyl 6-morpholinobenzofuran-2-carboxylate.

Workup

  1. temperatureafter heated
  2. temperaturereflux for 16 hours
  3. filtrationthe reaction solution was filtered
  4. concentrationthe mother liquor was concentrated under reduced pressure
  5. additionMeOH (100 ml) and concentrated hydrochloric acid (10 ml) were added to the residue
  6. temperatureafter reflux for 5 hours
  7. concentrationthe reaction solution was concentrated under reduced pressure
  8. additionA saturated NaHCO3 aqueous solution (100 ml) was added to the residue
  9. extractionto extraction with AcOEt
  10. dry with materialthe organic layer was dried with MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=5/1)

Sources & evidence

ORD record
ord-2e1c191d26224f9191abd7bf0624a99d
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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