4-Benzoyloxy-1-dimethylamino-1-hexene-3,5-dione → 3-(Benzoyloxy)-2-methyl-4H-pyran-4-one

HRID 466288Notes

Reaction equation

HRID 466288 reaction equation
[C:1]([O:9][CH:10]([C:18](=[O:20])[CH3:19])[C:11](=[O:17])[CH:12]=[CH:13]N(C)C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C>[C:1]([O:9][C:10]1[C:11](=[O:17])[CH:12]=[CH:13][O:20][C:18]=1[CH3:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 537626714-Benzoyloxy-1-dimethylamino-1-hexene-3,5-dione

Product 1

HCID 802553-(Benzoyloxy)-2-methyl-4H-pyran-4-oneYield 97.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Benzoyloxy-1-dimethylamino-1-hexene-3,5-dione (24.75 g, 90 mmol) is refluxed in 180 ml of acetic acid for 90 minutes. The reaction mixture is concentrated at 30°-35° C. on a rotary evaporator, the residue is dissolved in 200 ml of dichloromethane and washed twice with 100 ml of saturated sodium bicarbonate solution each time. The organic phase is dried over magnesium sulphate, concentrated on a rotary evaporator and gives 20.11 g (97.1%) of 3-benzoyloxy-2-methyl-4-pyrone. Content 86%, m.p. 106°-110° C.

Workup

  1. concentrationThe reaction mixture is concentrated at 30°-35° C. on a rotary evaporator
  2. dissolutionthe residue is dissolved in 200 ml of dichloromethane
  3. washwashed twice with 100 ml of saturated sodium bicarbonate solution each time
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-08e86760598b4e76a80b96fd4f5a55f3
Source dataset
uspto-grants-1992_10
Patent number
US05155254

Reaction notes

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