Acetic Acid → HCID 68227064, compound

HRID 403245Notes

Reaction equation

HRID 403245 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]([C:8](OCC)=[O:9])=[N:6][CH:7]=1.[O-]CC.[Na+].C(OCC)(=O)C.C(O)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[O:13][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:8]([OH:9])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2723922Sodium ethoxideHCID 68227270HCID 68227270, compound

Product 1

HCID 68227064HCID 68227064, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 5-chloro-3-(2-ethoxy-2-oxoethoxy)picolinate (385 mg, 1.34 mmol) in toluene (10 ml) at 23° C. was added sodium ethoxide (200 mg, 2.94 mmol) and the reaction mixture was stirred at reflux overnight. To the yellow suspension was added some ice, ethyl acetate and set to pH=4 with acetic acid. The organic layer was separated and washed with sat NaHCO3 solution. The aqueous layers were reextracted with ethyl acetate, then dried over Na2SO4, filtered and evaporated to give the crude ethyl 6-chloro-3-hydroxyfuro[3,2-b]pyridine-2-carboxylate (154 mg, 637 μmol, 47.6% yield) as a light brown solid. MS (ISN): m/z=240.1 [(M−H)−] and 242.3 [(M+2−H)−].

Workup

  1. temperatureat reflux overnight
  2. customThe organic layer was separated
  3. washwashed with sat NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-2348600b231548738baea38c501d2f82
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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