Lithium Hydroxide → HCID 89580475, compound

HRID 1501227Notes

Reaction equation

HRID 1501227 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([O:7][CH:8]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=2)[CH3:9])=[N:3][CH:2]=1.[OH-].[Li+]>CO.O1CCCC1.O>[N:1]1[CH:6]=[CH:5][C:4]([O:7][CH:8]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)[CH3:9])=[N:3][CH:2]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 89581345HCID 89581345, compound

Product 1

HCID 89580475HCID 89580475, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(1-(pyrimidin-4-yloxy)ethyl)benzoate (0.26 g, 1 mmol) in methanol (5 mL) and tetrahydrofuran (15 mL) was added lithium hydroxide (120 mg, 5 mmol) in water (5 mL), then stirred at room temperature for 5 hours. The reaction mixture was concentrated, the residue was acidified with 6 N hydrochloric acid, by filtration the solid was collected to give-4-(1-(pyrimidin-4-yloxy)ethyl)benzoic acid (0.19 g, 78% yield). LRMS (M+H+) m/z: calcd for 244.08. found 244.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationthe residue was acidified with 6 N hydrochloric acid, by filtration the solid
  3. customwas collected

Sources & evidence

ORD record
ord-490efab48b4845988bfeaefe706d87a7
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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