Acetic Acid → HCID 66991894, compound

HRID 1947233Notes

Reaction equation

HRID 1947233 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.[O:15]=[C:16]([CH3:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].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:17]([C:16](=[O:15])[CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 8868Ethyl AcetoacetateHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 66991894HCID 66991894, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5 g (26.57 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde, 3.4 ml (26.57 mmol) of ethyl 3-oxobutanoate, 1.9 ml (33.21 mmol) of acetic acid and 263 μl (2.66 mmol) of piperidine in 50 ml of anhydrous dichloromethane are stirred under reflux with a water trap for 24 h. After cooling, the solution is diluted with dichloromethane (50 ml) and washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. The residue is recrystallized from isopropanol. 7.63 g (91% of theory) of the title compound are obtained as an E/Z mixture.

Workup

  1. temperatureunder reflux with a water trap for 24 h
  2. temperatureAfter cooling
  3. washwashed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-87a9105e00af4e9b921b6c0076e879bc
Source dataset
uspto-grants-2013_03
Patent number
US08399471B2

Reaction notes

Loading…