Sodium Methoxide → 2-Methoxymethyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester

HRID 1242363Notes

Reaction equation

HRID 1242363 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:6][C:5]=1[CH2:20]Br.[CH3:23][O-:24].[Na+]>CO>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:6][C:5]=1[CH2:20][O:24][CH3:23]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67072139HCID 67072139, compound

Product 1

HCID 670723702-Methoxymethyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.401 g (1.072 mmol) of the above prepared 2-bromomethyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester, dissolved in 4.0 ml of abs. MeOH, was added 0.116 g (2.15 mmol) of sodium methoxide and the mixture stirred for 4 h at ambient temperature, when TLC indicated the complete disappearance of starting material. Pouring onto crashed ice/NH4Cl-solution, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=9/1), produced 0.279 g of pure title compound as white solid.

Workup

  1. dissolutiondissolved in 4.0 ml of abs
  2. additionPouring
  3. extractionextraction with AcOEt
  4. washwashing with water and brine
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-cca272acaad84bb6809b2c2af6e297d1
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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