Acetone → HCID 53729464, compound

HRID 542660Notes

Reaction equation

HRID 542660 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]([O:11][CH3:12])[C:8]([CH:13]=O)=[C:7]([O:15][CH3:16])[N:6]=1.[CH3:17][C:18]([CH3:20])=[O:19]>O>[CH3:3][O:4][C:5]1[N:10]=[C:9]([O:11][CH3:12])[C:8]([CH:13]=[CH:17][C:18](=[O:19])[CH3:20])=[C:7]([O:15][CH3:16])[N:6]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 112293762,4,6-trimethoxy-5-pyrimidinecarbaldehyde

Product 1

HCID 53729464HCID 53729464, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An aqueous solution of 2% sodium hydroxide (15 ml) was added to a stirred suspension of 2,4,6-trimethoxypyrimidine-5-carboxaldehyde (8 g) in acetone (15 ml) and water (15 ml). The mixture was stirred and refluxed for 4 hours, a precipitate slowly forming during this period. The suspension was diluted with water (100 ml) and extracted with chloroform (2×100 ml). The organic layer was washed with water, dried over magnesium sulphate and the solvent was removed by evaporation under reduced pressure to give 1-(2,4,6-trimethoxy-5-pyrimidyl)but-1-en-3-one as a pale yellow solid (8.0 g), mp 98°-99° C.

Workup

  1. temperaturerefluxed for 4 hours
  2. customa precipitate slowly forming during this period
  3. extractionextracted with chloroform (2×100 ml)
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d735c39c05124aae84b2910d7470f1d7
Source dataset
uspto-grants-1987_04
Patent number
US04659362

Reaction notes

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