Acetic Anhydride → HCID 10704487, compound

HRID 2288624Notes

Reaction equation

HRID 2288624 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N+:8]=2[O-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]([O:18]C(C)=O)=[O:17]>>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][O:18][C:16](=[O:17])[CH3:15])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 6036032-phenyl-6-methyl-pyridine-N-oxide

Product 1

HCID 10704487HCID 10704487, compoundYield 70%

Procedure

A stirred solution of the crude 2-phenyl-6-methyl-pyridine-N-oxide (5.2 g, 28.5 mmol) in Ac2O (25 ml) was heated at reflux temperature for 2 hrs. The Ac2O was removed with the aid of an oil pump (10 mm) at 40° C. to yield a red oil which was purified by flash chromatography over silica gel with Et2O/petroleum benzine=1/1 as the eluent and yielded 2-phenyl-6-(acetoxymethyl)-pyridine (4.6 g, 70%) as an oil.

Workup

  1. temperatureat reflux temperature for 2 hrs
  2. customThe Ac2O was removed with the aid of an oil pump (10 mm) at 40° C.
  3. customto yield a red oil which
  4. customwas purified by flash chromatography over silica gel with Et2O/petroleum benzine=1/1 as the eluent

Sources & evidence

ORD record
ord-4c0bd8a17de44d13a90cc2237c7abfec
Source dataset
uspto-grants-2000_07
Patent number
US06090812

Reaction notes

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