Water → HCID 18446294, compound

HRID 1269118Notes

Reaction equation

HRID 1269118 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:8]=[CH:7][N:6]=1)=[O:4].O.O.[OH-].[Li+]>C1COCC1.CO>[CH3:16][O: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 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 69472944HCID 69472944, compound

Product 1

HCID 18446294HCID 18446294, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(4-Methoxy-butyl)-pyridine-2-carboxylic acid methyl ester ((107 mg, 0.48 mmol, 1 equiv) in THF (1.5 mL) and water (0.5 mL) was added lithium hydroxide monohydrate (30.2 mg, 0.72 mmol, 1.5 equiv). The mixture was stirred at rt for 4 h and diluted with methanol (20 mL). Then H+ resin (0.4 g) 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 give 4-(4-Methoxy-butyl)-pyridine-2-carboxylic acid (63.4 mg, 63%): 1H NMR (300 MHz, CD3OD) δ 8.47–8.43 (m, 1), 7.98–7.94 (m, 1), 7.43–7.37 (m, 1), 3.41 (t, J=6.3, 2), 3.30 (s, 3), 2.75 (t, J=7.5, 2), 1.80–1.55 (m, 4).

Workup

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

Sources & evidence

ORD record
ord-339277b34e8e4964882f339386875218
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

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