Diketene → HCID 14950466, compound

HRID 1769069Notes

Reaction equation

HRID 1769069 reaction equation
[CH2:1]=[C:2]1O[C:4](=[O:5])[CH2:3]1.[N:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1>C(O)(=O)C>[CH3:15][C:14]1[O:16][C:2]([CH3:1])=[CH:3][C:4](=[O:5])[C:13]=1[C:10]1[CH:11]=[CH:12][N:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 805524-Pyridinylacetone

Product 1

HCID 14950466HCID 14950466, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Diketene (30 g) was added dropwise to a stirred solution of 1-(4-pyridyl)-2-propanone (20.25 g) in acetic acid (100 ml) at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 90 minutes. The mixture was heated to 50° and stirred for a further 90 minutes. The solvent was removed by evaporation and the residue purified by flash chromatography, eluting with dichloromethane/methanol (19:1 v/v) to give 2,6-dimethyl-3-(4-pyridyl)-4H-pyran-4-one (C) (21.6 g), as a yellow solid; NMR (CDCl3): 2.28(s,3H), 2.35(s,3H), 6.2(s,1H), 7.2(dd,2H), 8.65(dd,2H); mass spectrum (chemical ionisation, ammonia): 202 (M+H)+.

Workup

  1. temperatureThe mixture was heated to 50°
  2. stirringstirred for a further 90 minutes
  3. customThe solvent was removed by evaporation
  4. customthe residue purified by flash chromatography
  5. washeluting with dichloromethane/methanol (19:1 v/v)

Sources & evidence

ORD record
ord-164fcead701a499cbe73ccf3a44a95e5
Source dataset
uspto-grants-1995_01
Patent number
US05380730

Reaction notes

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