Acetic Anhydride → HCID 18629343, compound

HRID 1061453Notes

Reaction equation

HRID 1061453 reaction equation
C(OC(=O)C)(=[O:3])C.[Cl:8][C:9]1[CH:14]=[CH:13][N+:12]([O-])=[C:11]([CH3:16])[C:10]=1[O:17][CH:18]([F:20])[F:19]>>[Cl:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([CH2:16][OH:3])[C:10]=1[O:17][CH:18]([F:20])[F:19]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 86586467HCID 86586467, compound

Product 1

HCID 18629343HCID 18629343, compound

Conditions

Temperature
100 °C

Procedure

744 ml of acetic anhydride was added to 77.97 g of 4-chloro-3-difloromethoxy-2-methylpyridine N-oxide (VI), which was heated at 100° C. for 4 hour. The solvent was distilled off under reduced pressure and 2N sodium hydroxide was added thereto to adjust to pH 11 and the resulting mixture was heated at 100° C. for 1 hour. The resulting mixture was extracted with chloroform and the resulting organic layer was washed with saturated salt water and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; chloroform:ethyl acetate=5:1) to obtain 23.11 g of 4-chloro-3-difluoromethoxy-2-hydroxymethylpyridine (VII).

Workup

  1. distillationThe solvent was distilled off under reduced pressure and 2N sodium hydroxide
  2. additionwas added
  3. temperaturethe resulting mixture was heated at 100° C. for 1 hour
  4. extractionThe resulting mixture was extracted with chloroform
  5. washthe resulting organic layer was washed with saturated salt water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent; chloroform:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-5ba6818e40274e6ca11b734b1387c1f8
Source dataset
uspto-grants-2003_02
Patent number
US06525066B2

Reaction notes

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