Trifluoroacetic anhydride → 3,4-Dimethoxy-2-pyridinemethanol

HRID 1248306Notes

Reaction equation

HRID 1248306 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[CH3:14][O:15][C:16]1[C:17]([CH3:25])=[N+:18]([O-])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>ClCCl>[OH:4][CH2:25][C:17]1[C:16]([O:15][CH3:14])=[C:21]([O:22][CH3:23])[CH:20]=[CH:19][N:18]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydride2×HCID 107496473,4-Dimethoxy-2-methyl-1-oxo-1lambda~5~-pyridine

Product 1

HCID 107258093,4-Dimethoxy-2-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (4.0 ml) was added dropwise to a stirred solution of 3,4-dimethoxy-2-methylpyridine N-oxide (1.91 g) in dichloromethane (25 ml) and the mixture was left to stand at room temperature for 8 days during which time trifluoroacetic anhydride (4.77 ml) was added in two portions. The mixture was evaporated to dryness and the residue was purified by extracting a chloroform solution with aqueous sodium bicarbonate and elution from silica gel with methanol-chloroform (1:9) to give 2-hydroxymethyl-3,4-dimethoxypyridine (1.6 g).

Workup

  1. waitthe mixture was left
  2. additionwas added in two portions
  3. customThe mixture was evaporated to dryness
  4. customthe residue was purified
  5. extractionby extracting a chloroform solution
  6. washwith aqueous sodium bicarbonate and elution from silica gel with methanol-chloroform (1:9)

Sources & evidence

ORD record
ord-3229cffb1bb046c0b81fc11d5365a355
Source dataset
uspto-grants-1985_06
Patent number
US04523015

Reaction notes

Loading…