Acetic Anhydride → 2-(Acetoxymethyl)-6-benzoylpyridine

HRID 27936Notes

Reaction equation

HRID 27936 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[C:8]([C:16]1[N+:21]([O-])=C(C)[CH:19]=[CH:18][CH:17]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:5]([O:4][CH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:21]=1)(=[O:7])[CH3:6]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 545239806-benzoyl-2-methylpyridine N-oxide

Product 1

HCID 233378412-(Acetoxymethyl)-6-benzoylpyridine

Procedure

Acetic anhydride (6.6 ml) is heated to 115°, after which 6-benzoyl-2-methylpyridine N-oxide is added in portions over 1 hour. The mixture is then held at 115° for 1 hour after the addition. The reaction is poured onto ice and extracted with ether (3×). The combined ether phases are washed with sat. NaNCO3 (2×) and water until neutral, dried and stripped. The product is preparatory thin layer chromatographed, the least polar band giving 2-(acetoxymethyl)-6-benzoylpyridine.

Workup

  1. additionafter the addition
  2. additionThe reaction is poured onto ice
  3. extractionextracted with ether (3×)
  4. washThe combined ether phases are washed with sat. NaNCO3 (2×) and water until neutral,
  5. customdried
  6. customchromatographed

Sources & evidence

ORD record
ord-84043af643444024ae8c68d098aef509
Source dataset
uspto-grants-1980_09
Patent number
US04224330

Reaction notes

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