Water → 4-Hydroxymethyl-2-methoxy-3,5,6-trifluoropyridine

HRID 256162Notes

Reaction equation

HRID 256162 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([F:9])=[C:7]([F:10])[N:6]=[C:5](F)[C:4]=1[F:12].[CH3:13][O-:14].[Na+].O>CO>[OH:1][CH2:2][C:3]1[C:8]([F:9])=[C:7]([F:10])[N:6]=[C:5]([O:14][CH3:13])[C:4]=1[F:12]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 139851584-Hydroxymethyl-2,3,5,6-tetrafluoropyridine

Product 1

HCID 139851634-Hydroxymethyl-2-methoxy-3,5,6-trifluoropyridineYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.0 g (0.0055 mole) of 4-hydroxymethyl-2,3,5,6-tetrafluoropyridine (from Example 5) and 0.30 g (0.0055 mole) of sodium methoxide in 25 ml of methanol was refluxed for approximately twenty hours. After being cooled, the reaction mixture was poured into water. The aqueous solution was extracted with diethyl ether. The diethyl ether extract was dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated under reduced pressure, yielding 0.85 g of 4-hydroxymethyl-2-methoxy-3,5,6-trifluoropyridine as a yellow oil. The structure and nmr spectra are set forth in Table 1C below.

Workup

  1. temperaturewas refluxed for approximately twenty hours
  2. temperatureAfter being cooled
  3. extractionThe aqueous solution was extracted with diethyl ether
  4. extractionThe diethyl ether extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-196ca99cd6fc42e5bb3bc6aab511676f
Source dataset
uspto-grants-1987_10
Patent number
US04701464

Reaction notes

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