Sodium Chloride → Methyl 6-(hydroxymethyl)picolinate

HRID 744180

Reaction equation

HRID 744180 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](C2C=CC=CC=2)(C2C=CC=CC=2)[O:12][SiH2]C(C)(C)C)[N:6]=1)=[O:4].CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].[Cl-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][OH:12])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 131719562HCID 131719562, compound

Product 1

HCID 11513809Methyl 6-(hydroxymethyl)picolinateYield 63.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.52 g of 6-(diphenyl-tert-butylsilyloxymethyl)-2-pyridinecarboxylic acid methyl ester in 87 ml of tetrahydrofuran is mixed at 24° C. under nitrogen with 13.6 g of tetrabutylammonium fluoride-trihydrate and stirred for 2 hours. Then, it is mixed with 32 ml of concentrated sodium chloride solution and extracted four times with ethyl acetate. The combined organic phases are dried on sodium sulfate and after filtration, concentrated by evaporation in a vacuum. The thus obtained residue is purified by chromatography on silica gel. With hexane/50-100% ethyl acetate, 0.92 g of the title compound is obtained as colorless oil.

Workup

  1. extractionextracted four times with ethyl acetate
  2. customThe combined organic phases are dried on sodium sulfate
  3. filtrationafter filtration
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe thus obtained residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-bfa52026e7254c26b24c3bde7aea5814
Source dataset
uspto-grants-1996_09
Patent number
US05559134

Linked notes

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