Sodium hydride → HCID 58154771, compound

HRID 2359389Notes

Reaction equation

HRID 2359389 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([C:8]([O:10]CC)=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:13][C:14]1([CH3:21])[O:18][C@H:17]([CH2:19]O)[CH2:16][O:15]1.[H-].[Na+]>C1COCC1.[Cl-].[Na+].O>[CH3:13][C:14]1([CH3:21])[O:18][C@H:17]([CH2:19][O:1][C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH2:16][O:15]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 736056(R)-SolketalHCID 178468940HCID 178468940, compound

Product 1

HCID 58154771HCID 58154771, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Ethyl 6-hydroxypicolinate (500 mg, 2.7 mmol), (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol (1.11 mL, 3.0 eq) and NaH (60% dispersion in mineral oil, 385 mg, 3.3 eq) in THF was refluxed 18 hours. The reaction mixture was cooled to room temperature, acidified to pH=4, added to brine and extracted with ethyl acetate. The organic layer was dried, concentrated and recrystallized from pentane/ethylacetate to obtain (R)-6-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)picolinic acid (500 mg, 74% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customrecrystallized from pentane/ethylacetate

Sources & evidence

ORD record
ord-189ff6f923574cfda0ac0c91c765a085
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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