Lithium hydroxide, monohydrate → HCID 21076059, compound

HRID 1374467Notes

Reaction equation

HRID 1374467 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][F:15])[CH:8]=[CH:7][N:6]=1)=[O:4].O.[OH-].[Li+]>C1COCC1.O.CO>[F:15][CH2:14][CH2:13][CH2:12][CH2:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69469825HCID 69469825, compound

Product 1

HCID 21076059HCID 21076059, compoundYield 98.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(4-fluoro-butyl)-pyridine-2-carboxylic acid methyl ester (0.24 g) in THF (3 mL) and water (1 mL) was added lithium hydroxide monohydrate (71.3 mg, 1.7 mmol, 1.5 equiv). The mixture was stirred at rt overnight and diluted with methanol (20 mL). Then H+ resin was added and the mixture was shaken for 10 minutes. The resin was washed with methanol (1×), 1:1 acetonitrile/water (1×), and acetonitrile (1×). The product was eluted with 5% TEA in methanol (4×) and acetonitrile (1×). The combined organic solvents were evaporated and co-evaporated with toluene to provide 4-(4-Fluoro-butyl)-pyridine-2-carboxylic acid (0.22 g, 65%).

Workup

  1. additionThen H+ resin was added
  2. stirringthe mixture was shaken for 10 minutes
  3. washThe resin was washed with methanol (1×), 1:1 acetonitrile/water (1×), and acetonitrile (1×)
  4. washThe product was eluted with 5% TEA in methanol (4×) and acetonitrile (1×)
  5. customThe combined organic solvents were evaporated

Sources & evidence

ORD record
ord-9b831ea854a8419488599b02a11610f6
Source dataset
uspto-grants-2007_01
Patent number
US07164011B2

Reaction notes

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