Lithium Hydroxide → HCID 67520342, compound

HRID 1925324Notes

Reaction equation

HRID 1925324 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:20]([O-:22])=[O:21])=[CH:15][CH:14]=[CH:13]3)=[CH:5][CH:4]=1.[Li+].[OH-]>C1COCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([C:20]([OH:22])=[O:21])=[CH:15][CH:14]=[CH:13]3)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86608619HCID 86608619, compound

Product 1

HCID 67520342HCID 67520342, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(6-methoxypyridin-3-yloxy)-1-naphthoate (480 mg, 1.55 mmol) in THF (155 mL) at RT was added 1M aqueous LiOH (31 mL). The reaction was stirred until the reaction was completed. THF was removed in vacuo. The aqueous layer was acidified using 6M aqueous HCl to pH=6-7 and extracted with EtOAc. The aqueous layer was further acidified to pH=5 and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give the title compound, which was used without further purification.

Workup

  1. customTHF was removed in vacuo
  2. extractionextracted with EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fd122e1d23e4bd8823f20e08ec07f5f
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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