Acetic Acid → Propyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate

HRID 557416Notes

Reaction equation

HRID 557416 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.[C:15]([O:21][CH2:22][CH2:23][CH3:24])(=[O:20])[CH2:16][C:17]([CH3:19])=[O:18].C(O)(=O)C.N1CCCCC1>ClCCl>[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[C:16]([C:17](=[O:18])[CH3:19])[C:15]([O:21][CH2:22][CH2:23][CH3:24])=[O:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 74507Propyl acetoacetateHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 66991694Propyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Methyl-4-oxo-4H-chromene-8-carbaldehyde (2 g, 10.62 mmol) and propyl acetoacetate (1.53 g, 10.62 mmol) are dissolved in 500 ml of dichloromethane and, after addition of glacial acetic acid (0.76 ml, 13.28 mmol) and piperidine (0.1 ml, 1.06 mmol), heated under reflux with a water trap for 18 h. After cooling, the reaction mixture is diluted with 50 ml of dichloromethane and washed with 20 ml of sodium chloride solution, the organic phase is dried over sodium sulfate, and the solvent is removed in vacuo. 3.3 g (99% of theory) of the title compound are obtained as an E/Z isomer mixture.

Workup

  1. temperatureheated
  2. temperatureunder reflux with a water trap for 18 h
  3. temperatureAfter cooling
  4. washwashed with 20 ml of sodium chloride solution
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-cafa7b64f5284b6abafa92aae745538b
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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