2-Acetoxymethyl-4-cyclopropylmethoxy pyridine → 4-Cyclopropylmethoxy-2-hydroxymethylpyridine

HRID 1085108Notes

Reaction equation

HRID 1085108 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)[CH:9]=[CH:8][N:7]=1)(=O)C>[OH-].[Na+]>[CH:14]1([CH2:13][O:12][C:10]2[CH:9]=[CH:8][N:7]=[C:6]([CH2:5][OH:4])[CH:11]=2)[CH2:15][CH2:16]1

Participants

3

Reactant 1

HCID 156624932-Acetoxymethyl-4-cyclopropylmethoxy pyridine

Product 1

HCID 108450754-Cyclopropylmethoxy-2-hydroxymethylpyridine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To the crude 2-acetoxymethyl-4-cyclopropylmethoxy pyridine, NaOH (100 ml 2M) was added and the mixture was refluxed for 2 hours. The mixture was extracted with methylene chloride, and the phases were separated. The organic layer was dried with Na2SO4, filtered and the solvent was evaporated off, yielding 2.7 g of crude title compound. NMR data is given below. The crude product was used without any further purification.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. extractionThe mixture was extracted with methylene chloride
  3. customthe phases were separated
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-0bab58239c9e4a0dbd633075ff94882b
Source dataset
uspto-grants-1991_04
Patent number
US05008278

Reaction notes

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