Lithium Hydroxide → HCID 59526147, compound

HRID 385844Notes

Reaction equation

HRID 385844 reaction equation
C[O:2][C:3](=[O:14])[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[N:8]=1.[OH-].[Li+]>CO>[Br:13][C:9]1[N:8]=[C:7]([CH2:6][O:5][CH2:4][C:3]([OH:14])=[O:2])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58335249HCID 58335249, compound

Product 1

HCID 59526147HCID 59526147, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl[(6-bromopyridin-2-yl)methoxy]acetate (2.5 g, 19.2 mmol) in methanol (50 mL) was added aqueous lithium hydroxide (1M) dropwise over 15 min at 0° C. The reaction mixture was allowed to warm to room temperature overnight. The organic solvent was removed in vacuum and the residual aqueous solution was extracted with Et2O, and the aqueous phase was acidified to pH 2 with 1 N HCl. The aqueous phase was extracted with CH2Cl2 (3×100 mL). The combined organic extracts were dried and concentrated to afford the title compound.

Workup

  1. customThe organic solvent was removed in vacuum
  2. extractionthe residual aqueous solution was extracted with Et2O
  3. extractionThe aqueous phase was extracted with CH2Cl2 (3×100 mL)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bcb9f7c7ff2641df9f0ce6ffddd7adff
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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