Sodium ethoxide → Ethyl 3-hydroxyfuro[3,2-b]pyridine-2-carboxylate

HRID 1984287Notes

Reaction equation

HRID 1984287 reaction equation
C([O:3][C:4]([C:6]1[C:11]([O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=[CH:8][N:7]=1)=O)C.[O-]CC.[Na+]>C1(C)C=CC=CC=1>[OH:3][C:4]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:11]2[O:12][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

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

Product 1

HCID 54723935Ethyl 3-hydroxyfuro[3,2-b]pyridine-2-carboxylateYield 62.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 2-(2-ethoxycarbonyl-3-pyridyloxy)acetate (13.6 g, 54.0 mmol) and sodium ethoxide (8.08 g, 118.8 mmol) in toluene (200 mL) were heated under reflux for 18 h. After cooling, a precipitate was collected by filtration, dissolved in the minimum amount of hot water (about 300 mL), and acidified with acetic acid (6 mL). The resulting precipitate was filtered, and dried in vacuo to give ethyl 3-hydroxyfuro[3,2-b]pyridine-2-carboxylate as a solid (7.0 g).

Workup

  1. temperatureunder reflux for 18 h
  2. temperatureAfter cooling
  3. filtrationa precipitate was collected by filtration
  4. dissolutiondissolved in the minimum amount of hot water (about 300 mL)
  5. filtrationThe resulting precipitate was filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9727932f629a4caf890b9503a6e48525
Source dataset
uspto-grants-2009_06
Patent number
US07544693B2

Reaction notes

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