Sodium ethoxide → Coumaranone

HRID 1804632Notes

Reaction equation

HRID 1804632 reaction equation
C(O[C:4]([C:6]1[C:11]([O:12][CH2:13][C:14]([O:16]CC)=O)=[CH:10][CH:9]=[CH:8]N=1)=O)C.[O-]CC.[Na+]>C1(C)C=CC=CC=1>[O:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:4][C:6]=2[C:14](=[O:16])[CH2:13]1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 21793317Ethyl 3-(2-ethoxy-2-oxoethoxy)picolinate

Product 1

HCID 23556CoumaranoneYield 62.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 1.0 g (4.2 mmol) of the title compound from Step B in 30 ml toluene was added 2.9 g (9.2 mmol) of 21% sodium ethoxide. The reaction was refluxed overnight. After cooling down to RT, the reaction was filtered and the solid was collected. The solid was then dissolved in 20 ml water, and acidified by acetic acid. The solid was filtered and washed with dichloromethane and dried. The solid was added to 30 ml of 10% HCl aqueous solution and refluxed for 3 hr. Then HCl was evaporated to give 350 mg (62% yield) of the title compound. LC/MS: (M+1) 136.1

Workup

  1. temperatureThe reaction was refluxed overnight
  2. filtrationthe reaction was filtered
  3. customthe solid was collected
  4. dissolutionThe solid was then dissolved in 20 ml water
  5. filtrationThe solid was filtered
  6. washwashed with dichloromethane
  7. customdried
  8. additionThe solid was added to 30 ml of 10% HCl aqueous solution
  9. temperaturerefluxed for 3 hr
  10. customThen HCl was evaporated

Sources & evidence

ORD record
ord-dd0534ffc41248c988170d3a90675492
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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